


The World Looks Red

by twoheadedwoman



Category: Gilmore Girls
Genre: F/M, Literati (Gilmore Girls), Team Jess
Language: English
Status: In-Progress
Published: 2017-03-29
Updated: 2018-07-03
Packaged: 2018-10-12 12:03:21
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings, No Archive Warnings Apply
Chapters: 12
Words: 44,063
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/10490487
Author URL: https://archiveofourown.org/users/twoheadedwoman/pseuds/twoheadedwoman
Summary: An alternate universe where some things didn't happen but other things did and Jess sees Rory a lot earlier than the revival and they're both a lot more stable than you'd expect. Canon: Jess goes to therapy, lives in NYC, isn't completely miserable after all - Rory is single, a writer for the Times, and happens upon an record shop from her past.





	1. Wednesdays

**Author's Note:**

> This is my first fan fiction! None of these characters are owned by me.  
> Please give me lots of feedback for future chapters!!
> 
> ~eventual M because duh sexual tension for all~

Winter was Jess’ favorite time of year. The snow cloaking the city with a soft white blanket, the trees bare from their leaves, the fresh cold air stinging your face on a walk through the empty streets at night. He felt rejuvenated every winter, like he was new again. It had only been a couple of months since he decided to move Truncheon to New York City but everyday he felt like it was the best decision of his life. He missed the city he grew up with, it held so many memories for him and he was determined to only fill it with more. Luckily for him when Jess had approached Chris and Matt about moving they had already had the idea underway to expand as by this point their small publishing company wasn’t so small anymore. While Chris and Matt took care of the home front, Jess manned the NYC location with ease.  
He frequented a few of the same spots with a healthy dose of new ones as he began to feel not only more comfortable with the city but also more at home again. Upon his first week back, he ventured out and found that little record store he happened upon so many years ago with the one that got away. It was different, bigger, roomier, but still over-crowded with records that weren’t organized by genre but instead chronologically. This became his spot as he walked to Truncheon everyday and it was just around the corner. He came by everyday, looking through each year taking notes of interesting albums to eventually ask the owner about. He was an encyclopedia of music after all. Within the first couple of weeks this became his routine and he began bringing coffee to Freddy, resulting with long conversations about music, sometimes free records. When Freddy asks Jess to work for him, he’ s a little apprehensive, he doesn’t want to put his own business by the waist side, but the help was definitely needed and he agrees for mornings. He could use the extra cash.  
Fast-forward to a couple of months later and Jess is chuckling to himself as he walks to the shop on his coffee run, living above the record shop isn’t what he originally had in mind but its not only much cheaper(thank you rent control)its much nicer than what he originally found in the Bronx.

His routine was simple, work mornings at the shop and then head over to truncheon to edit, talk to authors, manage the general chaos - it was both anxiety-ridden and relaxing at the same time. It was a normal Wednesday morning, slow with the on slot of snow so Jess had lots of time to continue unraveling the nonsense order of vinyl Freddy left behind each day. He found more than a handful of unmarked boxes, he could barely hear the ring of the door each time someone walked in. He concentrated on the Breeders but could see someone in his peripheral view, “Hey let me know if you need any help,” he said briskly before lowering himself down again. The next time he looked up, he froze and his stomach dropped. “Hi…,” her voice a bit above a whisper, trapped in the same shocked daze as him. It took him a second to break his stare and catch his breath, “hi…,” is all he could muster as a response.  
She looked different. But only different in the way that she had matured, her innocence only replaced by confidence and grace. Her hair was longer, reaching almost her hips which were still slim and curvy, hugged by the cut of her jeans. He looked into those bright blue eyes and felt like the wind had been knocked out of him. Not exactly what he expected for a Wednesday morning. Embracing her was strange but welcomed, she smelled amazing.  
“What are you doing here?,” he says while easing himself out of the hug, unwilling to fully break free.  
Her hands lingered on his arm as she broke free, sending chills down his body. Her cheeks rose with that familiar blush, “Oh I’m looking for places to live actually…I just accepted an offer at the New York Times..,” she looks away with a shy humble tone, classic Rory.  
“What! that’s fucking amazing!” Jess didn’t mean for his excitement to escape him, but he genuinely was happy for her, even proud. Rory chuckled a little surprised by his earnest display of emotion, “Thanks! You’re the first person I’ve told, seems fitting.”  
Jess escorts them outside as they sit by the railing. “I’m honored,” he lights a cigarette to calm his nerves, he really wasn’t expecting this for a Wednesday or any day. Rory Gilmore in the flesh and he’s feeling 17 again. They sit in silence for awhile, “what a Wednesday,” she says while they catch each other’s eyes again.  
Jess smirks, “Yup.”  
“So, how long have you been working here?! How about Truncheon?! You weren’t the person I expected to see here. I mean not that it isn’t a welcomed surprise, its just been so long and I haven’t talked to you in so long and last time we talked you were still in Philadelphia. Oh, how’s Matt and Chris? Are they here too? Also, I read Ernest Hemingway recently and honestly, I still don’t see the appeal…”  
“Wow.”  
“What?”  
“I was waiting for that to happen,” he chuckles as she reddens again.  
“Sorry, I had a lot of coffee, I’ve been up since 6am and…”  
“No worries at all, it has been awhile. Um I’ve been here for a couple of months, I actually live right upstairs. We opened a sister shop here in New York since we had the means to expand and I’ve missed it so I decided to man the ship. Matt and Chris are still in Philly, but sometimes we switch depending on how restless we get and how business goes between the seasons. The real topic here is you read Hemingway?! I would’ve never expected that. I gotta say though he held a place in my teenage heart, I’ve decided to move on.”  
“Wow.”  
“What?”  
“I don’t know if I’ve ever heard you talk this much.”  
“It comes with age. I’m like a fine wine now.”  
“I’d say.”  
They lock eyes again. Jess smiles, a genuine smile as Rory does the same.  
“When do you start your job, Miss High Profile?”  
“In a couple of days, I gave myself some leeway to find a place, unpack a bit, explore a bit. It isn’t enough time but I’m too excited to wait.”  
“Rather just dive in. Definitely your style.”  
Rory looks at her phone as it vibrates, “Ugh, its my realtor.”  
As she answers the phone, Jess puts out the butt of his cigarette and stuffs his hands into his pockets. This feels familiar, yet new, like the last ten years have been a blur and they’ve been friends all along. But they were never truly friends, there was always a linger of more even as they’ve distanced themselves and become more estranged, picked up new lovers, shared the small tidbits of their lives by email - there was always more.  
“Unfortunately I have to go, we have an appointment in about half an hour and I have to make it up to Manhattan…somehow.”  
Jess nods, unsure how to end this whole surreal experience,”so…do we hug again or? Did we ever hug?”  
Rory laughs, “Well how about I give you my number and we catch up soon instead?”  
“Yeah, that sounds good.”  
As Rory enters her number into his phone, he’s close to her, he focuses on her features, still delicate and beautiful.  
She hands back his phone and catches him staring, “It was nice seeing you.”  
“You too.”  
“Bye Jess.”  
“Bye Rory.”  
She squeezes his arm once more and as she walks away. Jess goes back to work in a daze, feeling the faint phantom touch of her hand on his arm.

 

\---  
The days go by slowly and Jess replays their encounter in his head each time he goes down to the record store. He stares at her name in his phone and wonders if texting her is out of line, too soon, he overthinks every Hey it’s Jess that types out and deletes immediately. This is so stupid. She always made him nervous but never this nervous. They hadn’t talked in years. Or at least nothing past the occasional small talk when forced to be in the same room for birthdays, holidays, and now that Luke and Lorelei were together there was no hiding for either of them. They were civil, but estranged; Jess had forgotten the moment they shared in Philly, but the awkwardness lingered with Rory whenever she saw him. That same awkwardness lingering above him now. He decides to take the day off since the snow has deterred the usual regulars and occasional tourists from stopping by and heads to get a mid-day coffee in an attempt to drown his nerves in caffeine. He heads across town, the subway train has a hum to it that helps him relax and he’s finally able to focus on his copy of Edible Woman. The train fills up by the time he gets through to almost Manhattan completely forgetting his stop. He sighs as he looks up into the crowd that has suddenly engulfed his space and stops. There she is again, almost like clockwork for his anxiety. Her head also in a book standing by the doorway on the next car. Jess feels a slight drop in his stomach as he’s unsure of what to do, he regrets not attempting to contact her sooner, realizing how awkward this situation is. As he contemplates getting out at the next exit, she must have felt his stare since she suddenly looks over at him, her face already breaking out into a smile as she waves at him. He gives an awkward smile and waves back as she slowly makes her way through the crowd.  
“Well isn’t this a surprise,” she says as she finally reaches him.  
“Sure is,” he says dryly trying to hide his emotions.  
“Where are you heading? Seems a bit farther than your usual destination unless you’ve secretly starting working in Manhattan.”  
“Nah, I took the day off from the record shop and it hasn’t been my day for writing so I decided to get some coffee but somehow missed my stop so..here I am,” he unintentionally unloaded all this on her and realized how uncool he felt in that moment. This really wasn’t his day.  
“Oh well, I’m just getting off work for the day and was going to grab a bite before I headed home..would you like to join? Unless you’re completely dedicated to missing your stops and reading Atwood by yourself then by all-means don’t let me interrupt.”  
She was quick and witty, just as he remembered her. Her forwardness caught him by surprise, he liked it, this new trait that older Rory had.  
“Uh yeah, as long as there’s coffee involved I could accept this invitation. Hopefully I’m not interrupting your time with…wait is that On the Road? I didn’t think I would ever see you with a copy of that in my life.”  
“Excuse you, this isn’t my first rodeo! Besides, its not for pleasure, its for business. I’m interviewing a writer who takes himself as the new Kerouac and figured I would at least try to find a way to enjoy it.”  
Jess laughed, “Wow, harsh.”  
“Sorry, its been a day.”  
“Tell me about it.”  
“I will. This is our stop, there’s a really good italian restaurant right around the corner from my place, i could use a lot of pasta. And bread. Lots of bread.”  
“Glad your appetite hasn’t changed.”  
“I have quite a refined palette now, thank you.”   
They stepped out of the train and both layered on their jackets, beanies, and gloves before leaving the station. They walk silently for a couple of blocks as they readjusted back to the freedom of the sidewalks and the cold air on their faces. Jess glances over at her, watches her determined face, recognizes it instantly as the same one that she always had when she had a lot on her mind.  
"So..I read Fountainhead recently," he figured he would try to revert back to the normal, to what they could always talk about with each other.  
"What! Wow, you write three books and you finally decide to evolve your reading material huh?" she teases as she nudges his arm with hers.  
"Hey, I like to think that it was an act of desperation as I read it on a train-ride going to Seattle and it was the only good book in this sketchy bookstore I passed through North Dakota. That was only after I wrote Subsect so joke's on you," he nudged her back as she giggled getting a rise out of him.  
"Jess Mariano, stubborn as always, but at least well-read," she smiled over at him. Her face was flush, her cheeks and nose rosy, she still had that innocent look about her. 

He couldn’t shake the sound of his heart pounding in his ears.


	2. This friendship thing

**Summary for the Chapter:**

> Jess hosts an event and the reunion is in full swing. A new friendship begins.

“So wait, Lane thought she was pregnant but that was a fluke and she had an epiphany while listening to PJ Harvey to leave Zack and move to NYC?”  
“You’ve got the gist of it. Crazy right?! And she reconnected with Dave since he also lives here, they’ve been inseparable ever since.”  
“Geez, its an all around reunion now.”  
“I swear this was completely unplanned and coincidental.”  
“Are you sure you didn’t drug my pasta and plan on kidnapping me into your cult?”  
“There’s no getting past you,” Rory said laughing while waving her napkin in surrender.  
“I’m honestly more surprised that you ate a salad with all that. I don’t think I’ve seen you eat a green food item in my life.”  
“Hey, I told you my palette is refined now!” she threw her napkin at hime while Jess dodged it with his hands up.  
“Oh sorry, I forgot you’re a part of the elite now, must come with the package,” Jess deadpanned while throwing the napkin back at her.  
“Please interviewing faux-Kerouac writers for small columns is hardly elite, they gave me the scraps,” Rory sighed while sipping her wine glass. Jess looked at her with sympathy.  
“We all gotta start somewhere. You made it from the bottom before, you could do it again.”  
“I know, I just feel like I’m starting at square one again. I’m 27! Its too late for me.”  
“Gilmore, you’re 27…You’re not a grandma. Spare me.”  
“Hey!” She giggled. “I’m ready to retire.”

Jess felt comfortable. The last two hours went by in a flash and he couldn’t believe he was nervous in the first place. This was Rory Gilmore sure, but it felt like the lost time between them dissipated.  
“I can’t believe its already 3,” he said while looking at his phone, messages and missed calls from what Matt and Chris.  
“Sorry, did I hold you up?”  
“Oh no, not at all, I just kinda left the office without telling anyone, Matt and Chris are in town. They have dependency issues, its fine.”  
“You didn’t tell me that! Its okay if you have to go, I live close by, I have wine at home to keep me warm.”  
“Rory, its fine, we just have a party tonight at Truncheon, release of a book, its kinda a tradition of ours,” Jess reassured her while looking over the check.  
He looked over at her, “You should come through. Well if you’re not busy. We usually go down to this bar and do karaoke-“  
“Wait, Jess Mariano doing karaoke? Say no more. I’m meeting up with Lane tonight and I’m sure she’d love to witness that,” Rory rubbed her hands together in mischief.  
“No one said I would partake in such, just that its there. You’d really need to liquor me up for that. I may or may not have sang Bruce Sprinsteen in the past, but there’s no evidence of it so.”  
“Wow, well I’ll change my rsvp from yes to maybe Mr. Grumpy Pants,” she pouted.  
“Mr. Grumpy pants, that’s me.” Jess smirked while rolling his eyes. They split the check and walked back into the sharp cold air.  
“Which direction you going?” Jess asked while unpacking a cigarette.  
“I’m just a couple blocks this way, you should come by! I know you have to get going, but you should really see my apartment…and I may or may not need help lifting a bed frame from the lobby…”  
“Oh I see how it is now. Feed me then use me. And here I thought this was totally innocent.”  
“Well what else are you going to do with those muscles!” Rory said it matter-of-factly.   
“You’re right, you know I think I’ve been training for this exact day,” Jess said while dodging Rory’s incoming hand to the arm and walking in her direction. 

Rory opened the door to her apartment. They walked in among a maze of boxes that were expertly organized throughout each room.  
“Okay don’t judge it too harshly, I’m still unpacking of course.”  
“I just carried this bed frame up three flights of stairs, its too late for judgements.”  
“I swear I had no idea the elevator was broken!”  
“Uh huh,” Jess sighed while dropping the heavy box with the others.  
“This is nice, didn’t think I’d see your bedroom past Yale paraphernalia and floral comforters.”  
“Oh yeah, grown up Rory is real minimal, all boxes. I even own a can opener.”  
“Huh. I like it.”  
Rory offered a cup of water to Jess as they sat on the couch.  
“I like this,” Rory said after a long pause of silence.  
“Like what?” Jess asked shifting through a box of books in front of him.  
“You being here. Or I don’t know this weird coincidence that you’re involved in. I felt nervous coming to New York and you being here..helps me feel comfortable.” Jess felt his face redden, he took a sip of his water taking in her response, unsure how to untie his tongue.   
“Yeah. I like it too,” he said while looking over at her. His leg began to shake out of habit and he realized their knees were touching.   
He rose suddenly, “So I have an appointment to get to before tonight..”  
“Oh yeah, thanks so much for having lunch with me and for your muscles. Or I mean your help. I’ll see you tonight?”  
“Definitely. And no problem at all. I’ll let myself out.” Rory walked him to the door and they exchanged a hug. Still a foreign exchange of contact to Jess.  
“Bye Jess.”  
“Bye Rory.”  
—————————

“You haven’t brought up Rory in awhile, how do you feel now that she’s suddenly back in your life?”  
“Honestly, its a strange feeling. Its definitely sudden. It feels familiar, but different. Like the kind of comfort you find at the top of a roller coaster before you take the plunge down.”  
“Mhm. So you’re excited for this, welcoming it even?”  
“I guess, I’m not really ready for it. But I’m open…”  
“Good. Being open is important, your vulnerability has really helped you over the years. Remember, try not to equate your worth to the past. That’s what you told me your goal was right?”  
“Right. I know. Its..hard for me.”  
“You’re doing great,” Dr. Flint said while jotting down notes,”Your progress is not small feat, don’t sell yourself short Jess.”  
“Mhm.”  
These hour sessions each week helped Jess center himself. When he moved to Philly he felt like he had all his plans set and figured out, but he quickly realized he needed to change, to open up, be vulnerable. It started as a goal for writing, then therapy really made him let go of his anger, forgive the past, and move on. Each week he felt less tense as he walked out of Flint’s office. He was ready for that plunge, he was happy where he was in his stability and having Rory in his life - no matter their dynamic - was truly welcomed.  
—————————

He changed when he got back home. Combed his hair which was almost at his shoulders, trimmed his beard, and looked through his flannel. He layered a checkered red one over a thermal and black tshirt. He quickly laced up his boots and cuffed his jeans, grabbed his leather jacket and was out the door. He waved a goodbye to Freddy on his way out through the shop.   
The party had already started by the time he go there, he was always the one to show up fashionably late. He gave handshakes and hugs to almost everyone while walking down the halls and avoided Matt and Chris’ judgmental looks as he neared them.  
“Way to answer your phone!”  
“We thought you had died, we were worried sick,” they were both buzzed and ready to roast him.  
Jess rolled his eyes, “Relax mom and dad. Everything looks up to speed. Its not like we haven’t done this countless times before.” He poured himself a whiskey on the rocks.  
“Yeah no thanks to you. Where were you though? I know you had your session but c’mon, you seem too happy.”  
“Don’t worry, I didn’t smoke any weed with the hooligans at the playground. I was out in Manhattan, had lunch, ran late and still made it here.”  
“Right. Its a girl, I knew it,” said Chris while Matt shook his head.  
“We really thought you changed young man,” Matt teased wagging his finger.  
Jess laughed,” Jesus, fuck off.”  
Chris was right, but Jess didn’t want to give him that satisfaction just yet. Truthfully, Chris and Matt will be dumbfounded when they find out Rory was his lunch date. They had both sworn to exile her from all conversations after witnessing Jess’ hurt years ago in Philly despite his reassurance that everything was forgotten. They were there for him during his string of flings in the aftermath and his more recent serious breakup a year ago, so he really didn’t have the heart to tell them just yet. They moved through the halls and upstairs, greeting new and old clients as well as authors, along with possible networks for profit. The beginning of the night was Jess’ least favorite part. He found networking boring regardless that his charm and skill made him really good at it. Usually after the book reading, the crowd would thin out and he could loosen up his professionalism.   
Each time the crowd shifted he would look for Rory. A couple of hours went by and he worried that his invitation was tossed aside. He hated feeling invested already so he drank another whiskey to relax. As he sat down for the reading on the sidelines he recognized Lane and Dave with Rory right behind quietly seating themselves in the back. Rory looked around and caught his eye with a smile and small wave, he waved back as Lane and Dave did. he took a couple of deep breaths and tried to keep his cool, leaning back into his seat.  
——————————

The reading went by quickly or it felt like it to jess who couldn’t focus now that he felt his old friends in the room. After the Q and A, Matt made his last announcements of the night and invited who left to OMiley’s down the block.  
“Jess! This is amazing! There’s so many people here!” Rory had a genuine look of pride and excitement. Jess smiled as he greeted them.  
“Yeah people still come to these for some reason,” Jess teased dryly while looking around.  
“I’m glad to see your sarcasm aged well, its nice seeing you,” Lane commented as they hugged. Regardless of her past perspective of Jess, they had become civil over the years, even engaging in talks about music and books when they would see each other around Stars Hollow.  
“You too. Hey Dave, its been awhile,” he said patting Dave on the back and clinking their red cups together.  
“So are we all going down the street or?” Rory said while moving around and dodging people in the room.  
“Yup, just gonna clean up with Matt, but I’ll see you there in a bit.”  
Okay but you better not leave, I already told everyone that you’re s pro at karaoke and they can’t think I’m a liar, I have a reputation to uphold,’ she exclaimed while gripping his shoulders.  
“Relax, get a hold of yourself Gilmore,” Jess put his hands to hers, lingering for a moment before removing them. “Your rep already may be tarnished since I made no promises.”  
“Ugh fine. See you over there Mr. Grumpy Pants,” Rory rolled her eyes as they moved along with the crowd out the door.

Matt looked over from the reading room while folding chairs,” Jess, wait, was that?” Jess looked over at him with a questioning look, attempting to avoid the subject altogether.  
“So I’m just going to clear the other room..”  
“No no you’re not getting out of this. Was that Rory?! I don’t think I smoked enough pot to imagine that.”  
“It was her, yeah…its a long story..”  
“You’re telling me everything!” Matt demanded while they cleared the other rooms together.

It was hot, loud, and over-crowded by the time Matt and Jess made it over to O’Miley’s. He had taken off his thermal in anticipation for the crowd, he expected the atmosphere and he didn’t entirely hate it. They walked in just in time to see Lane and Dave singing together to Weezer’s Buddy Holly, Rory watching among the already wasted audience.   
“Jess! You didn’t tell me Rory was here, I thought we were brothers!” a drunk Chris appeared, putting his arms around Jess’ shoulders.  
“What? I can’t hear you! I’m getting a drink!” he could hear him just fine, he wanted to avoid the repeat warnings he already heard from Matt. He ducked out of Chris’ grip and headed for the bar.  
He walked over to Rory after ordering a whiskey but was interrupted by a familiar brunette and her friends.  
“Ah Jess Mariano, thought you would be here,” it was Marie, a reoccurring fling Jess had over the years. She was a beautiful woman that he had met at Truncheon; olive skin, green eyes, long dark hair.  
“Marie, what are you doing here? i thought you moved back to Philly?” Jess looked over at Rory who had an awkward look on her face as she waved at him.  
“i did, I’m just in town for a couple of nights. I heard Jess was finally single,” she said as she brushed her hand on his hip. Jess hitched his breath at the contact.  
“How about we catch up another time. Trying to do the networking writer thing.” Truthfully she had an intoxicating quality to her, but he was trying to move past bad habits, especially ones involving emotionless sex. Marie followed his eyes to Rory and sighed.  
“Oh, I didn’t know I was interrupting anything. You know my number.” Jess nodded at her and walked away.  
“Hey, did I miss any ballads from you yet?” He asked while finally making it to her table.   
“I’m having a hard time choosing between Rush or Journey.”  
Jess cringed,”how will you ever choose.”

The night progressed with more drinks as Jess felt the tension mount from Marie and Rory being in the same room. He had no shortage of alcohol as friends and coworkers alike kept buying him them. He went outside for a cigarette, regretting his decision to shed down to a tshirt but too impatient to look for his jacket.   
“I was wondering where you went,” a wobbly Rory came to his side.  
“I’m pretty drunk, can’t really think in there. Or at all right now,” Jess laughed while trying to light his cigarette with little success. Rory grabbed his lighter and helped him out.  
“Jess, is this okay?”  
“This. Us. Friends.”  
“Rory, you really gotta help me out with this one.”  
Rory sighed,”This. Everything. Like being back in your life. Being friends even if I was terrible to you.”  
“Oh,” Jess contemplated this over, unwinding the feelings he was trying to bury the majority of the night. “I mean, its a lot yeah, but don’t you think if I didn’t want you in my life again I wouldn’t have invited you here? You’re not a bad person Rory. We both made mistakes. Me, a lot. But I didn’t invite you here to guilt-trip you.” He was surprised he was able to articulate his thoughts since Rory was close enough for him to focus on the lining of her lips.  
“I’m sorry. For everything.”  
“Me too.”  
They stood silently for awhile letting their apologies hang between them.   
“Well I think its time for me to close out the night,” Jess finally said while smirking at Rory.  
“What?!” she chased after him into the bar.  
Before Rory could even get to the stage, Jess was giving his speech,”This is dedicated to Truncheon and everyone still standing in this room. And Matt who is sleeping in that bar stool.” He was staring directly at Rory as he began to sing Jail Break by Thin Lizzy, head banging with every guitar riff, and nailing the air guitar along with it. The crowd sang along each time Jess pointed the mic at them and cheered when it ended. Rory stood there laughing and clapping.  
“I love drunk Jess!” yelled Chris.  
“This is amazing!” yelled Lane in response.  
As Jess drops the mic in tandem with the end, applause spreads across the room. Rory gaps at him with a wide smile.  
“You’re still a surprise to me!”   
“I’ll regret this tomorrow.”  
“Especially when you see the footage,” Rory says menacingly.  
“No you didn’t,” Jess reaches Rory’s hand, trying to grab her phone. She switches it to her other hand while their limbs become entangled. They laugh and pause as they catch their breath, Lane and Dave interrupting their stare.   
“Jess what the hell you should’ve been in our band in high school!” Dave exclaims.  
“Yeah we could’ve really made it,” a wobbly Lane agrees.  
“I’m sure we would’ve been the next Nirvana,” Jess pats them on the back.  
The bartender calls out the last call while they decide to head out the door.  
“Is the subway even running at this time?” Rory bundles up while walking outside.  
“Yeah, but you’re going the opposite direction from us..I think?” Lane replies looking confused. “We’re in Bedstuy, you could catch a cab with us if we could find one…”  
“Well you could all stay at my place, there’s plenty of room,” Jess offers while looking over at Rory.  
“Only if its not any trouble.”  
“Not at all. Its a couple blocks this way.” They all stumble their way over to his place, trying not to slip on non-existent patches of ice.   
Jess opens up the front gate to the apartment building attached to the shop. He opens the multiple locks and steps in, they walk up the steps and down the hall.   
“Well this is it.” The apartment is spacious, the size of a flat with multiple filled book shelves to the ceilings and make-shift record boxes lining the walls.  
“Whoa, grown up Jess is real high fidelity. Cool.” Dave says while looking through his records.  
Jess quietly laughs and gets them all cups of much needed water, then finding blankets for the couch.  
“Rory you and Lane can take my bed, Dave the couch, and I’ll take the chair.”  
“Jess no you should have the bed, I can sleep pretty much anywhere.”  
“Please. Its not a big deal.”  
He leads Rory to the bedroom and its bathroom.  
“Here I have an extra toothbrush.” He hands her one as they brush side by side.  
Rory giggles and mumbles something with a mouth full of foam.  
Jess spits, “What? Sorry not understanding this language.”  
“I was just remembering you singing. You really have the dark mysterious punk persona down,” she teases.  
“Glad I’m finally understood.”  
They walk out into the living room to find Lane and Dave passed out on the couch.  
“Huh. That was literally five minutes,” Jess sighs as he places a blanket over them,  
Jess brings a blanket over to the chair.  
“You could share the bed with me..”  
Jess stops and turns to Rory taken aback by her suggestion.  
“Its freezing in here, the bed is big enough for two.”  
“Rory..”  
“Jess, lets not make it a thing. Just sleep next to me and be comfortable in your own home,” Rory wasn’t going to take no for an answer. Jess wondered why she was so adamant about it.   
“Uh okay sure.” They go to his room and shut the door. The last time they were on a bed together was at Kyle’s party, where everything unraveled between them. The circumstances were much different now.   
Jess hands Rory a pair of shorts and a tshirt, “figured you didn’t want to sleep in jeans.”  
“Thanks,” she changes in the bathroom while he does in the room. He turns off the light and gets into bed, leaving a large space for Rory to crawl in, he decides to face the wall. He isn’t entirely ready for this, but keeps his composure, as a friend would. The bathroom door opens and he feels Rory lay next to him, her warmth immediately in the sheets.   
“Goodnight Jess.” He can feel her breath against his back despite the space between them. The hair on his neck stand up.  
“Night Rory.”  
His heart is back in his ears and he eventually drifts to sleep  
——————

The next morning is hazy, Jess wakes up abruptly forgetting for moment the body entangled in his limbs. Rory’s head is on his chest and their legs are intertwined. This is a foreign feeling, but entirely comfortable. Just like they’ve always been. Jess looks down at Rory, still asleep breathing heavily against him. He brushes hair out of her face softly, not wanting to wake her. He lays there awhile, both not wanting this moment to end and not entirely sure how to get out of it, but decides to avoid the potential awkwardness and slowly unties his legs from hers. He moves his arm under her while lifting her head with the other. He’s facing her now, the window’s light brightening her face, so angelic and beautiful. The urge to kiss her is overwhelming, he bites his lip to stop his thoughts. Rory turns over at the change of position and Jess reluctantly gets up.  
He heads quietly into the kitchen and gets a pot of coffee going while Lane and Dave still sleep without a stir. He sits down with his book at the counter and hears a thud shrugging it off, but then hears his door open to his room. He turns to see a blanket wrapped Rory bleary-eyed and wobbling out of his room, sitting next to him at the counter.  
“Hmph.”  
“Good morning.”  
“Who evens wakes up this early on a Saturday.”  
“its 10am.”  
“Exactly!” she puts her forehead on the table.  
“I forgot the Gilmores don’t do mornings. Coffee?”  
She nods her head, her head still down. He places a cup of coffee by her side, Rory slowly lifting her head and picking it up. Jess watches her and smirks, noticing the change of expression on her face instantly.  
“Better?”  
“Mhm,” she smiles at him.  
“Jesus, what time is it!” Lane exclaims from the blanket bundle on the couch.  
“10am..”Jess repeats.  
“Ughhh.”  
He gets more cups of coffee and puts it on the table by Lane and Dave.  
“How are you not hungover?!” Lane glares at him while he walks back to the counter. Jess laughs and shrugs at her.

They all finish their coffee while discussing the night before, filling in details that they weren’t sure actually happened. When they finish, Lane and Dave decide to leave as they both work afternoons at separate coffee shops while Rory stays behind leafing through Jess’ books.  
Jess closes the gate before Lane and Dave and heads back into the apartment to find Rory still in his shorts and tshirt looking through his shelves.  
“You still write in the margins.”  
“Yup. Old habit I guess.”  
“I do too,” she smiles.  
“So..what do you have planned for today?” He asks after a long stare between them, he’s still at the door keeping distance between them.  
“I think I should finally get around to unpacking boxes at my place.”  
“Ah over the minimalist lifestyle already?”  
Rory giggles,”Yeah, it just wasn’t for me. What do you have planned?”  
“Not much, probably going to a show tonight for some locals bands. Work a bit at Truncheon catching up on what I neglected during the week. Go to the gym…”They were sitting next to each other on the couch, separate blankets between enwrapping them.  
“The gym?! also do you ever rest?!” she exclaimed and Jess laughed.  
“I’ll sleep when I’m dead or whatever they say. I like to keep busy.”  
“Well..I guess I should get dressed and get on my way.”  
“Right.”  
“Jess.”  
“Yeah?”  
“Can we do this again? I mean the hanging out thing? I really had a good time and I really like this whole..friendship thing we have going on.”  
Jess smirked,”Of course. Friends. Thats how it works”  
Rory smiled back at him and they sat in silence for awhile contemplating this new stage of their relationship they haven’t experienced before.


	3. Warm snow

**Summary for the Chapter:**

> Jess and Rory head to Stars Hollow and exchange some new memories.

**Notes for the Chapter:**

> This is still a slow burn, its been really difficult for me not to automatically make this a Literati porno lol. I decided to make this chapter a little shorter in order to build up/also to just focus on the bridge moment - let it warm your insides a bit ;)

Rory became a regular part of Jess’ life in the weeks to follow the infamous karaoke party. When they weren’t grabbing quick lunches when possible, Rory would bring afternoon coffees to Jess’ side of the city, catching up on their day’s events or discussing their daily books. They would mingle in each other’s friends’ groups, even crashing at each other’s places if alcohol inhibited their ability to travel. Jess was grateful for this change, regardless if his feelings for Rory only grew stronger the closer they became.

“So you’re telling me you’re just friends,” Matt began on an early morning at Truncheon, sitting next to Jess in the reading room while he looked over edited pages on his laptop.  
“Yes.” Jess said irritated.  
“So you haven’t kissed or touched in any way?”  
“No.”  
“So you’re telling me you aren’t constantly flirting obviously in front your friends who have known you for years?”  
“Jesus, why am I getting this third degree right now? its barely 9am, lay off will you,” Jess got up and left the room. It was a regular occurrence that either Matt or Chris annoyed him, but they’ve been relentless since Rory came around.  
He went upstairs and through the main editing hall, it was a busy Monday and each desk was already filled by editors and publishers. Jess moved down the hall greeting those whose doors were still open until he reached his office at the end of the hall. He made sure to lock the door behind him this time. He finally was able to concentrate with headphones in blaring David Bowie, the usual classics usually pulled him through his least interesting edits. As soon as he was in his zone, he could hear the door knock loud enough to break his concentration.  
“Go away!” he yelled at the closed door.  
“Hey, its me!” It was Rory, she was here strangely early. He looked at his phone while getting up, not missing any phone calls from her.  
“Hey, sorry, come in.” He moved to the side as he let Rory in to sit down.  
“Sorry, I totally came without notice and you’re obviously busy but I was told to come get you and apparently its an emergency but they aren’t telling me what’s going on and I left early from work so I could come here and I’m kinda freaking out a little-“  
“Rory.”  
“Who even calls someone with “Its an emergency, get Jess, come as soon as possible”? A sociopath thats who-“  
“Rory!”  
“What?!”  
“Breathe. I need more details here. Preferably calmly.”  
“Sorry. Okay, Kirk called me, which is isn’t weird in itself, but weird nonetheless. But he told me there was an emergency and that I needed to get you and to come to Stars Hollow as soon as possible,” she sighed finally calming down in her seat.  
“Kirk? Huh. Well..I guess we better go?”  
“Thats your reaction? This could be so many things! What if Luke and Lorelai are hurt? What if we’re getting pranked? What if the diner is on fire? and you’re just like “Huh.”” She mimicked him and couldn’t hide her overall panic.  
“Well, its not out of the ordinary for Stars Hollow. Relax, I’ll drive.” He looked over at her and tried to soften her glare with a smirk.  
“Ugh. Fine.”  
“Maybe we can get some ice cream while in town. It’d really cement this whole twilight zone vibe we got going on.” Rory nudged him while they walked downstairs.  
Bye lovebirds,” Chris said while Matt held back a laugh. Jess shot back a death stare when he opened the door.

“Wait, do you have a car?”  
“I do, its in the garage. I just don’t really use it unless I’m leaving the city.”  
They walked to the local garage down the street. Jess knew the old man who owned it for years so he was able to convince him to leave it here in exchange for a couple of bucks here and there.  
“Ah, don’t have your piece of junk anymore?”  
“Nah, it died a couple years ago. Lots of memories there, I miss it sometimes until I realize it could’ve killed me if I kept driving it.”  
“Definitely lots of memories,” Rory smiled as they entered the car, preparing for their trip to Stars Hollow.  
“I’m telling you twilight zone.”  
The drive to Stars Hollow was easy, no traffic after commuting hours, and the snow was light for mid-January. Conversation was easy as usual, even though Jess felt a little less secure driving next to Rory. He couldn’t help but feel deja vu of that fateful car-ride they took that took an awful turn. Literally. But then again, he always felt deja vu with Rory. He always bounced back to memories of being 17 and completely smitten. The feelings were the same even though the years have past.  
“Where’d you go?” Rory said looking over at him.  
“What?” Jess said confused.  
“You just went totally silent for a second,” she laughed looking at him perplexed.  
“Oh, nowhere, must have zoned out.”  
“You don’t have to be nervous Jess.”  
She was good at that. Knowing how he felt even when he didn’t say anything. Even when he tried really hard to have a neutral face to the world around him, a hard shell.  
He couldn’t help but smirk at her, “Can’t help it. Not trying to break your arm again.”  
“I think we’ll be okay. It seems like you’re a lot more responsible more. I mean, we aren’t going for ice cream when you should be studying.”  
They both laughed at that simultaneously.  
“I was an idiot.”  
“Me too. Its okay,” she reassured him.  
Before they knew it, they pulled into Stars Hollow. The town was covered in a layer of soft snow looking like a postcard from another timeframe. Unlike New York, the townspeople looked happy walking in the snow, the weather never changed their routines. They pulled into the Gilmores’ driveway.  
“Home sweet home. Are you coming?”  
Jess sat there, unsure if he really wanted to get out of the car. He reluctanty opened the car door and stepped out to Rory’s side.  
“You know, I don’t think my mom hates you anymore. I mean, she knows I’ve been hanging out with you. Plus, you’re a long way from a black eye Jess.” She smiled over at him and they stepped onto the porch and she reached into her pocket to get her keys.  
“Well as long as that’s cleared up.”  
Before Rory could put the key into the lock, the door swung open.  
“Loin fruit!” Lorelai yelled as she grabbed her daughter into a hug.  
“Hi mom,” a muffled Rory said into her arms.  
Jess awkwardly stood there as they embraced, an awkward Luke approaching the door. They made eye contact and gave each other the same side smirk waiting for the embrace to end.  
Luke cleared his throat, “Lorelai..”  
“Oh god, I’m sorry, I must have blacked out. Its been so long!”  
“Mom it been maybe a week.”  
“Its been so long!” she repeated as they all entered into the house, sitting in the living room.  
“You both look great.” Luke said breaking the silence that suddenly entered the room.  
“Okay, you two almost gave Rory a heart attack with your ambiguous message so please spare us small talk.” Jess said annoyed.  
“Okay okay we’re sorry, we weren’t sure how to get you both here together without some sort of mystery,” Lorelai said smiling. “So…we wanted to tell you two the news first, especially after the first time this happened..”  
Jess and Rory looked at each other, more confused than this morning.  
“…We’re engaged!!”  
“Oh my god!”  
Rory got up and immediately hugged her mom, they erupted into a cluster of nonsense high-pitched noises. Jess got up and hugged his uncle.  
“About time old man,” he teased.  
“We realize the first time this happened, it wasn’t the best timing and our relationship was reminiscent of a David Lynch movie and I married Chris temporarily..”  
“Mom..”  
“But we set a date for next month and we’re making it happen, its been five years, we’re ready.” Lorelai smiled as she looked over at Luke.  
“I’m so happy for you two!” Rory exclaimed again.  
“We need to go celebrate! To Luke’s!”  
“Oh c’mon,” Luke sighed reluctantly as Lorelai and Rory were already out the door.  
Jess and Luke were left walking alone to the diner.  
“So.”  
“So.”  
“What’s going on with you two?” Luke questioned.  
“What are you talking about?”  
“Jess.”  
“What?”  
“I see the way you look at her.”  
“I have no idea what you mean.”  
“Jess..”  
“Uncle Luke…”  
“Look, I know you don’ t want to hear this. But I’m going to say it anyway because you’re stubborn as hell. Don’t wait. Don’t be me. You need to tell her how you feel or else you’re going to have to deal with your heartache every time you see her with someone else. She’s special and so are you. Please don’t wait,” Luke was serious, he had stopped completely on the sidewalk at this point to tell Jess holding onto his arm.  
All Jess could do was nod.  
The rest of the walk there was mostly silent as Jess contemplated Luke’s words. He knew he was right, but he was honestly scared he would fuck everything up again.  
“Thanks…” he said eventually not looking over at Luke.  
“If you ever need to talk about it…” Jess smirked at how his uncle had not changed much and how it took him so long to realize how similar they were. He nodded at him again before they entered the diner.  
The Gilmore Girls were sitting at their regular table in the corner, they were deep in conversation as the two of them walked in.  
“Finally! We’ve only been waiting a lifetime!” Lorelai said impatiently waving a menu in the air.  
“Relax. Its been what, a total of five minutes,” Jess rolled his eyes. It really felt like old times, like he was back working at the diner again.  
“Shush Bukowski, lets eat,” Lorelai and Rory ordered their usual grand slam breakfast of pancakes, eggs, sausages, bacon, waffles, french toast, just about every breakfast item on the menu. Jess and look just ordered a bagel and fruit.  
“What?” Jess asked as Lorelai and Rory eyed him down.  
“Fruit? what kind of monster are you?” Rory exclaimed.  
Jess smirked and shook his head.  
They spent a good two hours at the diner, drinking endless coffee, and catching up. Jess and Luke mostly stayed quiet unless asked a direct question. Lorelai was unusually chatty with Jess, as unusual as it can be for someone who talks so much, asking him questions about New York, Liz, his sister, etc. basically any topic she could think of. He tried not to feel uneasy, as they’ve had conversations over the years, and ultimately reached a civil consensus - even enjoying each other’s presence at get-togethers as they shared a similar sense of humor, but being the center of attention was never his forte.  
After eating he decided to step outside for some air as a light snow began to fall, he walked over to the old bridge he used to escape to for peace. There wasn’t one part of Stars Hollow that didn’t hold memories for him and this one held the most. He waved to Patty and Babette on his walk over who didn’t hold back on commenting on his more “rugged” appearance, he tried to wave to Kirk who instantly ran in the opposite direction upon seeing him, and he even attempted a wave at Taylor though it was obvious to him Jess would always be the town hooligan. He laughed to himself at his accomplishment. Jess had cleaned himself up over the years, the majority of the town had welcomed his return especially after becoming a published author and paying back Luke - he wasn’t sure how that got around. He had also both finished his GED and degree two years ago, the only person he told being Luke, Matt, and Chris.  
He sat down on the bridge and looked down at the frozen water, as much as he disliked Stars Hollow for its bitter memories, he still enjoyed its winter. He took out a cigarette, his first of the day.  
“You know if Taylor sees you smoking that, he’s going to hold a town meeting in your honor,” Rory said while sitting down beside him.  
“Perfect for my reputation,” he replied while lighting it.  
“I thought I’d find you here.”  
“Just needed a break.”  
They sat silent for awhile, staring up into the falling snow.  
“Feels different here now that I’m older,” Rory said while still staring up.  
“How so?” Jess looked over at her, admiring the way the snow set onto her long hair.  
“Just..different. It feels like this place I made up as a child or teenager as a haven for when I felt upset or scared. I guess its pretty similar now, but I just go here for peace and quiet. Plus there’s all the memories..” she looked over at him and caught his eye.  
“Lot of those..”  
Rory put her hand over his and looked up to the sky again. He laced his fingers with hers and sighed quietly at the warmth.  
“Rory!” Lorelai yelled, foot steps coming closer. She let go of Jess’ hand slowly and put her hands in her lap, Jess doing the same. His heart felt it was going to burst out of his chest, as if they were caught in Luke’s apartment attempting their first kiss.  
“Hey there you guys are! We thought you left! I gotta go back to the Inn since Sookie needs backup and I’m sure both of you have plenty of things you rather be doing than staying in Stars Hollow for the day.” She looked at the two of them, Jess felt like he’d been caught.  
“Oh sure, yeah we should probably get back to the city,” Rory replied while getting back up, he reluctantly followed.  
“Sounds good. Gotta say bye to Luke real quick.”  
They all walked over to the diner and said their goodbyes for now. Lorelai held onto Rory a little longer as Luke and Jess exchanged a hug.  
“I know you still hate it here but you’re always welcome.”  
“Thanks..Uncle Luke,” Jess replied while smiling.  
Rory and Jess headed towards the car, “So..ice cream?”  
“How can you even think of ice cream with all you ate a couple of hours ago?”  
“I’m already starving, plus its ice cream!”  
“I knew you were the rebel this whole time.”  
“Thats me, fuck studying.” They laughed together as they got into the car.

“I hope they don’t take as long as we did,” Lorelai said while watching them leave from the diner door.  
“Yeah. We all know Jess is Rory’s me,” Luke replied smiling as they looked towards one another and exchanged a kiss.  
\----------  
Rory drove on the ride back to New York, she was filled with sugar as she had devoured a triple scoop with ease. Jess reminisced on their shared moment on the bridge but didn't dare to bring it up as he wasn't entirely sure what it all meant. He delved into his book while simultaneously replying to Rory's constant banter about the engagement, the wedding to come, Stars Hollow.  
"What do you have planned for the rest of the day?" she asked as she pulled up in front of her apartment  
"Uh I guess trying to finish what I left. Lots of boring editing."  
"Do..you have any plans for tonight?"  
"For a Monday? not really. I'm not a Monday night party person."  
"Well...there's this event that my work is having and I was going to invite you to come earlier but wasn't sure if it'd really be your thing but I also didn't want to go alone so I was wondering if you wanted to stop by? You don't have to stay long, you can really just eat all the free food you want and you don't have to mingle with me or anything."  
"Okay."  
"Okay? Okay. Great. That was easier than I thought, you aren't as stubborn as I remember you," she laughed, her shoulders relaxing and easing off the steering wheel.  
"Sounds fun. Plus I get to see the type of rich people you work with. Thats always fun," Jess deadpanned.  
"Its not totally the most yuppie place you could be, I promise. You do have to kind of dress up though.."  
"Oh, I thought I could just get away with a tshirt and jeans, you didn't tell me there was a dress code. Might have to decline."  
"There's no backing out now!" Jess smirked at her and she relaxed, not picking up on his sarcasm this time.  
"You're the actual worst," she laughed.  
"Its my charm. See you tonight," he said while Rory closed the car door and waved at him while she walked into her apartment.  
He definitely needed another cigarette.


	4. Lady Stardust

**Summary for the Chapter:**

> Jess gets out of his shell, confessions and memories are shared..among other things.

He went through his small selection of button-ups over and over. They were all fairly similar, some plaid, some plain, he wasn’t sure if he could pull it off either way. He felt more nervous than anticipated and was regretting accepting the invitation altogether. He didn’t necessarily care that he would be in the company of New York Times staff, it was more so that Rory had invited him to this at all, the hand-holding and this was a lot to process missing the times in his life that were more filled with teen melancholia than actual anxiety. He felt like he was going soft and wasn’t sure if that was an improvement in the Rory department, but here he was. He settled for a black button up over a some dark grey slacks and hoped that his boots wouldn’t blow his cover, he pulled out a peacoat from the back of his closet, pulling it altogether wasn’t half-bad though he felt like he was entrenched in a costume.  
He headed out to Manhattan to meet Rory at her place. He couldn’t focus on his book the whole ride there and put in his headphones out of frustration trying to at least concentrate on My Bloody Valentine as best he could. By the time he made it to Rory’s, the sun was setting and he had completely forgotten what time he actually needed to be here, hoping he wasn’t too early or late. Rory rang him through the front gate and he made his way upstairs, the elevator finally working, he couldn’t stop fiddling with his fingers. When Rory answered the door, Jess’ breath hitched, he was hoping it wasn’t audible. She was wearing a form fitting dark red dress that stopped above her knee, a neckline revealing her collarbones and plunging just a bit down her chest; she was absolutely sexy and he was trying hard not to be too obvious when he was checking her out.   
“Uh hi,” was all he could muster.  
“Hi,” she smiled,”oh come in. I’m almost ready so you’re right on time.”  
There she was gauging his feelings again.  
“He sat down on the couch as Rory disappeared into the other room. He hadn’t been in her place since it was filled with boxes, it was completely organized now. Decorated with prints and shelves of books, and pictures. He got up and looked at the pictures above the fireplace, picking one up of Rory and Lorelai at her high school graduation. He recalled calling her that day and being too nervous to say anything, instead letting her hurt hit him full on after he’d left with no warning to California.  
“Ready. You clean up nicely.” He turned putting the picture down.  
“You too,” they smiled at each other.  
“So, shall we?”  
They headed out the door and caught a cab outside. The event was nearby but Rory was wearing heels in the snow and there was no way she could walk without slipping.  
The wine bar they went to was large and elegant, Jess had never stepped into a place like this let alone ever wanted to. There were people lining every corner and the in-between, huddled in groups, an obvious means of networking. They walked straight to the food table, Rory saying hi to everyone they walked by but determined to eat first. They picked their food, Jess’ a mere snack plate in comparison to Rory’s.  
“Usually they have us go to a fancy restaurant, but I prefer this atmosphere I think. I feel at least a little more normal here.”  
“Yeah, the tea sandwiches are definitely rustic.”  
They ate observing the crowd when an older man walked up to Rory with a group of what seemed to be his entourage in tow.  
“Rory! You have people to meet, come!”   
Rory turned to Jess but couldn’t manage to say anything without being whisked away, only able to send him a sympathetic look while mouthing “sorry.”  
Jess awkwardly stood by the food table suddenly feeling like a black sheep in the crowd as he looked over at different people, mostly women, staring him down like vultures. He walked over to the bar and sat in the far, less crowded, corner.   
“So you’re Jess.”  
“What?” he looked up startled and found a tall slim woman with long blonde hair and intense green eyes looking directly at him.  
“You’re Jess Mariano, the writer for Subsect right?”  
“Um yes. Sorry, who are you?”  
“My apologies, I’m Laura, Rory told me about you, we work together.”  
Jess was still unsure why she was talking to him at all, but he shook her hand anyway.  
“I just saw you here and figured I would come over and say hi since it seems like you were abandoned and I also hate these sort of events. Hopefully I wasn’t interrupting anything.”  
“Not really. Just my plate of food here.”  
“Well, I’ve read your books over the years, so I was surprised to hear that Rory knew you. Maybe we can set up an interview, we’re always looking for more independent off the radar writers.”  
Something about Laura reminded him of Paris, she was very direct and forward, maybe even a little rude about Rory. Though her presence seemed more catty than deliberate.  
Before Jess could answer, Rory walked up out of thin air next to his side.  
“Hi Laura, how are you?” Jess noticed a different tone in Rory’s voice. She didn’t like this woman at all.  
“Hi Rory, good good. Just talking to Jess over here.”  
They smiled at one another and stared. Jess looked back and forth between them, feeling like he could cut the tension between them with a knife.  
“Uh so how was it over there?”  
Rory changed her expression as she turned to him,”Oh you know, not super fun, but a necessary evil. What were you two talking about?”  
“Laura here was talking about a possible interview. I guess the Times needs more independent writer stories..”  
Rory turned back to Laura and they continued their stare.  
“Well thats always a good idea.”  
Laura nodded, “Here’s my card Jess. Let me know if you have any time to continue talking.”  
He took it,”Will do.”  
She walked away and Rory’s stare intensified.  
“This is getting a little West Side Story, you doing okay?” He noticed a jealous look in Rory’s eyes, he had unintentionally made her jealous of Laura. Though he was sure it wasn’t entirely his fault he was long past the days of having a Shane and trying to get Rory to dump Dean.  
“Yeah, she’s kind of my reival? I’m really not into competition with other women, especially after graduating high school and dealing with Paris as a arch nemesis for so long. I tried being her friend but she’s not having it. So she’s gotten under my skin and she’s trying to bring you into it which is just..great. I’m sorry,” she was rambling and obviously a little taken aback from this whole interaction.  
“Hey, its okay, if it makes you feel any better I’d definitely hit you up for an interview over her any day.”  
“She wasn’t trying to interview you, or maybe she was, she’s trying to literally get in your pants.”  
“…Huh. I guess I didn’t pick up on that. She was pretty monotone..”  
Rory’s face was red and clearly upset at this point, he wanted to comfort her, but also felt confused why she was all of the sudden so territorial over him.  
“Lets get out of here.”  
“I can’t, I have to stay here. I don’t want her to see how I left early and didn’t network or anything.”  
“I feel like you’ve earned your place here. She’s obviously threatened by you. Let’s go.”  
“Where?”  
“Anywhere. I know a place,” he smirked at her, trying to change her expression, she smirked back at him.  
——————  
“How’d you know a cart hotdog would make me feel better?”  
“Do you feel better?”  
“A little.”  
“Okay, I got another stop then.”  
They walked into a liquor store and Jess bought an array of junk food snacks and beer. Rory looked at his questionably but didn’t say anything. He unlocked the record shop store front, letting them in. He picked out The Rise and Fall of Ziggy Stardust… by David Bowie and put it on, he brought out a blanket for them to sit on and turned on the heater so they wouldn’t freeze.  
“Make-shift night time picnic, okay I feel better.”  
“Its almost like I know you or something.”  
“Thanks Jess. Really, this turned my night around,” they clinked their beers together.  
“I have something to confess to you,” Jess said after a long silence of them being heavily involved in their thoughts.  
Rory sat up and looked over at him,”Oohh I didn’t know we were doing truth or dare.”  
“Not so much that. Just figured we could reach new territory in our friendship and build trust ya know.”  
“Okay, what is it?!”  
“So remember when I had that black eye and told you I got it from playing football..”  
“Wait..that was a lie?”  
“Yeah. I mean did you really believe it anyway?”  
“No, but what happened then!”  
“So..a swan at the lake hit me in the eye…”  
“A swan.”  
“Yeah. A swan.”  
“Hit you in the eye.”  
“Yes.”  
“A swan hit you in the eye and gave you a black eye.”  
Jess rolled his eyes at Rory who was trying really hard to keep back her laughter with no avail. He laughed with her, getting over the moment of embarrassment he just revealed.  
“I slept with Dean,” Rory blurted out as Jess almost choked on the beer he was sipping.  
“What?” he coughed looking over at her.  
“He was married and I slept with him. It was a bit after Liz’s wedding. It was a huge mistake.”  
“Didn’t expect this. Definitely beats my story.”  
Rory looked down in shame, she wasn’t kidding, or remotely amused at her confession.  
“I slept with my therapist. Not my current one, but back in Philadelphia when I first sought it out. It lasted a couple of months before she basically turned herself in for it.”  
They both sat in silence as they thought over this landslide of truth before them.  
“We’re both pretty fucked up, huh?” Jess said finally.  
“Yeah must be why we work so well together,” Rory giggled.  
They looked at one another, Jess had the urge to kiss her, but instead got up and flipped the record to stop himself. He didn’t want to ruin this. They carried on until 2am, reminiscing and allowing themselves to open up more to one another.  
“Geez, its late..I should probably get home.”  
They both got up and reluctantly walked out the shop door so Rory could wait for a cab. Rory was shivering slightly, Jess handed her his jacket.  
“Now you’re going to be freezing.”  
“Nah, I’ll be fine.”  
She smiled at him as they waited together.  
“Do you ever think about it?” Rory asked.  
“About what?”  
“How it would be like to try this again?”  
Jess paused looking over at Rory who was already staring at him.  
“All the time,” he answered honestly. There wasn’t anything to lose at this point of the night, they’ve shared so many memories as it is, he didn’t want to relive the past, but he did want to make a new future. If possible. Just then the cab pulled up and they hugged, they pulled away slowly their faces a couple of inches from each other. They shared one single kiss before Rory opened the door to the cab.  
“Bye Jess,” she said while she got in.  
All he could do was wave and smirk at her. He stood there frozen for what seemed like forever as he watched the cab take a corner. He finally caught his breath, his heart beating in his ears again.


	5. Glow

**Summary for the Chapter:**

> Some relieved tension, but mostly lots of feelings.
> 
>  
> 
> *I apologize for any errors in this, I needed to get this done but its soo late! Hopefully it was worth the wait <3

Jess couldn’t sleep well the days following their kiss. Each night he would toss and turn for hours only to have slept 3-4 hours, if anything, he woke up each day to go to the gym and exert his tension but to no avail. He couldn’t help thinking that he had ruined it, their friendship, the possibility of a relationship. He couldn’t help thinking about how he wasn’t over it all, even though its been so long. He was beginning to think that this was the end, even before it really had the chance to begin.  
He headed to his therapy session which couldn’t come at a better time, he was anxious and couldn’t open himself up to Matt and Chris considering his track record with Rory. Dr. Flint was unbiased and though Jess was still getting used to being entirely vulnerable in front of another person, he could unload his anxieties without judgement.  
“Why do you think you ruined this?” Dr. Flint asked Jess who was having a difficult time putting his feelings into words this morning.  
“This is just what always happens with us. I tried this so many times and it always turns out this week. I should have stayed friends with her. She doesn’t owe me anything.”  
“Well, you’re right, she doesn’t necessarily owe you a romantic relationship, but this kiss you shared seemed reciprocal. You can’t base the present on the past. I know its difficult for you, but it seems like Rory and you have made progress is doing so.”  
“I know..I know”  
“Have you contacted her?”  
“No.”  
“Jess. Communication seemed to be a huge issue in your past. You’re a lot different than the monosyllable person who walked into this office a year ago. Do you think being honest and upfront with your boundaries would be useful in this case?”  
“Yeah. But its Rory. What if I lose her entirely?”  
“It may have to be a risk you take, but avoiding it entirely didn’t do much good before, right?”  
“Right.”  
Jess had a lot of processing to do. What Dr. Flint advised him on wasn’t entirely rocket science, but it helped to have someone be there to guide him in the process. He didn’t want to resort back to running away from Rory, which was an obvious roadblock in their relationship both past and present.  
He typed and erased a Hey in a text messaged multiple times before it seemed ridiculous. He left his phone on the counter instead, deciding to not send anything, if she wanted to talk to him, she would.  
He headed to the shop and decided to take the day off from Truncheon which Matt and Chris weren’t excited about, but didn’t have much of a choice since Jess was technically the boss. He asked Freddy if he could take over for the day which he had no qualms about.  
———————————————  
He engulfed himself in 90s grunge records while organizing and it was surprisingly busy for a Tuesday afternoon, so the hours past him by. He felt more at ease after talking to Dr. Flint, even if he was unsure how to proceed, he tried not to be overcritical with himself.  
He looked up almost simultaneously as Rory walked in and he could feel an imaginary lump begin to form in his throat.  
“Hey,” she said while bringing coffee.  
“Hey,” he replied, unsure of what else to say.  
“I brought coffee. Figured you could use it, its a lot busier than I thought it would be for a Tuesday.”  
“Yup, the one day I take over for Freddy and this happens,” he was wondering if she was going to ignore the kiss between them. Maybe it didn’t feel as important to her as it felt to him. Maybe her body didn’t feel like it was on fire and ice cold all at once. Maybe those feelings had faded for her.  
“I’m guessing this isn’t the best time to talk then?”  
“No. Its fine, we can go to the back.”  
They walked into Freddy’s small office and Jess closed the door as they awkwardly sat down and looked at each other, that familiar tension looming between them.  
“So, about last night..”  
He waited for her to continue as her cheeks redended and he held his breath.  
“I’m sorry for unloading all my past issues on you. I wasn’t sure if that was necessarily the most appropriate thing to do especially the Dean thing…I’m going to blame excessive alcohol and junk food, but also I’m getting really comfortable with you and its a little scary.”  
“Scary?” he interrupted, not too keen to hear that word.  
“I mean, this is a little scary for me. I can’t forget our history and the more I hangout with you the more I reminisce on our past.”  
His heart sank into his stomach.  
“I’m remembering all the good parts and its been a lot easier for me to let go of any grudges I had with you since you’re so much different now..obviously. The last couple of weeks I’ve been really happy to have you in my life.”  
She looked directly at him and he was unsure if she expected a response but instead let her continue.  
“I’m going to be leaving for a couple of months after the wedding. I was offered a job on the west coast to interview a bunch of independent writers…”  
“You’re leaving.” Jess looked down, he couldn’t hide that this news saddened him. He was used to having Rory around.  
“For six months..”  
He nodded. Six months wasn’t the longest, but it was disappointing nonetheless.  
“And our kiss…”  
They looked at each other again, they had the same look in their eyes. The wanting, the inevitable lust they’ve built up over the years, the spark of a possible love.  
“I’m sorry its always such bad timing for….this.”  
“Yeah. Me too.”  
“So I think its best for us to remain friends,” Rory said this while biting her lip as her eyes welled with a hint of tears.  
“Thats okay. I mean..I can’t say I’m not disappointed, but we both have lives to live and I don’t want you to feel pressured in any way while you’re gone.”  
“And I don’t want you to feel pressured while you’re here. But I still want you in my life.”  
Jess gave her small smirk, it was all he could manage at this point. He reached over and wiped away a tear that began to roll down Rory’s cheek with his hand. She smiled at him.  
“So…did Dave text you about tonight?” Jess asked.  
“Oh yeah, his show, are you going?”  
“Yeah..are you?”  
“I think so. VHS Vengeance, not the best band name, but I’m hopeful,” she laughed.  
Jess felt a sense of relief even though the news wasn’t exactly how he wanted to it to pan out, he rather have Rory in his life in some way rather than not at all. He had three weeks to be around her as much as he could before she left for half a year, he didn’t need to be bitter.  
—————————————  
Jess arrived at the show as he planned, catching the beginning of VHS Vengeance’ set just in time. He spotted Rory in a corner with Lane, Matt, and Chris, and a couple of faces he didn’t really recognize. He bought a drink and made his way over, being that Dave’s band was relatively new, their set lasted a total of 15 minutes which included bits of conversation with the crowd.  
“Good set. You sound like a mixture of Nirvana meets the Melvins if they decided to go the shoe gaze route,” Jess commented as Dave was packing up.  
“I’m glad someone sees the vision,” he replied laughing.  
They walked over to their group of friends and Jess saw Rory talking to a man he had never seen before, he was particularly close to her, he could feel a rise of heat in his stomach. The only person he ever really became jealous over was Rory and that didn’t seem to change over the course of 10 years.  
“Hey!” Rory looked over at him, she was considerably more drunk than he’s seen her recently, but he also forgot that she was a light weight. She hugged him by surprise and pulled away before he could embrace her, all very awkward. The man behind her was looking at him questionably, he returned the look.  
“Jess, this is my coworker Oliver and my other coworker who you might remember Laura.”  
“Hi,” he raised his hand.  
“Oh, the writer that Laura wouldn’t stop talking about?” Oliver asked giving Jess a condescending smirk.  
Jess’ jaw tensed as he stared at Oliver; he was around Jess’ height, dark blonde hair, and blue eyes, he reminded him of the blonde dick from Yale so he already didn’t like this guy, add in the elite smug writer personality and he was done. Laura was also pretty drunk as she wobbled over like a new born giraffe to Jess, he was assuming that Rory and her had smooth over their rivalry but still noticed as Rory glared at her as Laura placed a hand on Jess’ shoulder.  
“Sorry. Your shoulder is really strong,” she gripped it to keep her balance.  
“Uh, thanks. I guess.” He felt extremely awkward and excused himself to get a drink.  
He waited at the bar to order as Rory sat down next to him.  
“Sorry about..all of that. They tagged along as I told them I was going to this and wouldn’t really take my passive aggressive body language for a no so here I am two whiskey and cokes later trying to relate to these people..”  
“Huh. Seems about right. I see your arch nemesis is here.”  
“Yeaaah, she’s okay, she’s very much my new Paris, but slightly scarier if that is possible.”  
“Chilling,” he smirked at her.  
“Sorry about Oliver…”  
“What do you mean?”  
“I mean, he’s honestly kind of an asshole, so I’m sorry in advance if he’s the worst. He was being pretty condescending back there. I can tell he was sizing you up. He really has no chance so I don’t know why he’s bothering.”  
“No chance, huh?”  
Rory’s face turned red as she took a sip from her drink.  
“I don’t know,, maybe you should give him a chance, the whole asshole thing didn’t stop you before,” he teased her as she turned and hit his arm.  
“Rude!”  
They walked over to their booth, now filled with Dave and his bandmates, Jess sat next to Laura reluctantly as she checked him out with no shame, luckily Rory sat on his other side. The booth was tight so their knees and arms touched, heat radiating onto each other. Jess felt like his skin was on fire and ice cold at the same time again. Rory got up and went with Lane to the bathroom, freeing up a little space in the booth. Oliver looked at him with judgement, he swore he could see his nose turn up. Jess’ jaw tensed as they stared each other down from across the table.  
“Laura wouldn’t stop talking about your book, whats it called? The Subside?”  
“The Subsect, you know that Oliver!” Laura exclaimed.  
“Right. It was..pretty good. Are you writing anything else of that genre or are you over your male protagonist self-filling prophecy?” He was trying to push Jess’ buttons and doing a good job.  
“Nah, I think there aren’t enough male characters in this world, ya know?” Jess deadpanned, having the urge to punch this guy was overwhelming.  
Oliver scoffed,”Oh, that was a joke.”  
“What the fuck is your problem?” Chris asked from down the table.  
Rory and Lane walked up to take their seats, looking at their friends and realizing they walked into something not entirely unexpected.  
“Hm, should I give you both guns to draw or is this more of a Westside Story type of deal?” Matt asked as he looked from Jess to Oliver, neither of them flinching.  
“What’s up, you guys?” Lane asked awkwardly.  
“I’m fine. How are you doing?” Oliver asked with a slight smile.  
“Fine,” Jess replied, there was something about him that made his blood boil.  
Jess loosened up as Rory sat beside him, accidentally placing her hand on his leg which almost made him choke on his beer.  
“Sorry,” she whispered to him.  
“It’s okay,” he whispered back, his fingers grazing hers, she didn’t move her hand entirely as it laid next to his by their knees. He blamed their lack of inhibition on alcohol, though he knew that he wasn’t entirely unaware of what he was doing. He felt slightly threatened by Oliver, who spent a lot more time with Rory and held a Yale degree. He remembered the moment that Rory told him she was in love with Logan, the pang in his entire body was a feeling he’ll always remember. They agreed to be friends and assumingly date other people, he was hoping he could move past his own jealousy in order to solidify that agreement.Though that was proven to be easier said than done.  
Jess decided to head home with Matt and Chris in tow, he was reluctant to leave at first, especially with a drunk Rory in the hands of Oliver but Lane caught onto his concerned looks and told him she would look after her.  
Matt and Chris hassled Jess on the whole subway home, luckily their stops came before his.  
He was left with his thoughts and luckily a book to occupy his hands when his phone vibrated.  
Seriously so sorry about Oliver. I owe you!!!!  
He smiled, regardless of how drunk Rory was she was still able to send a coherent text message. She was still thinking of him.  
————————————————  
The two weeks before the wedding went by quickly. Jess spent a lot of his free time in Stars Hollow, helping out Luke who was especially anxious. While in town, he slept at the old apartment above the diner and helped Luke open up each morning, it was bittersweet for him, remembering high school and how much of a fuck-up he was. He was always trying to make it up to Luke who took years to accept the check he offered him in Philadelphia. He began to enjoy the scared stares he received from Kirk, how Taylor had gotten over thinking of him as a hoodlum and wouldn’t stop talking to him about his writing, and still felt uncomfortable being stared and giggled at by the town’s high school girls whenever they came into the diner.  
“Whoa, deja vu,” Rory said while she walked in.  
“Right? still waiting for that vortex to open up. What are you doing here?”  
“Probably the same thing you are, helping my mom with the wedding. She’s turned into what they call a bridezilla except she’s only really worried about the amount of food that will be there and whether or not she should let Kirk sing covers of the Cure.”  
“Sounds about right.”  
Jess placed a giant cup of coffee in front of her with a danish. He watched as she giggled as his gesture.  
“What?”  
“Nothing. Are you sure your name isn’t Luke now?”  
“I would ask if your name is Lorelai now, but it is actually is so..”  
She laughed as she heard Miss Patty and Babette come in.  
“Oh my god! Its like a blast from the past!”  
“I’m pretty sure I’ve been seeing you all week Babette,” Jess said getting ready to roll his eyes.  
“Yes you, but you two together? Its like some sort of miracle. Weddings really bring the love together,” she exclaimed while looking between them both with a ridiculous cartoony smile and raising her eyebrows.  
“Geez,” Jess scoffed while walking away to help with orders.  
“My, you really have matured,” Miss Patty said as he walked out. She was blatantly checking him out as he bent over, he had almost forgotten about the obvious harassment.  
“Patty, Babette, can we get you anything or is harassing my nephew enough?” Luke said walking behind the counter.  
“Well he is a plate and a half these days..”  
Jess sighed louder,”Luke..”  
“I can take over from here.”  
“No, I wanna help you..just rather not be getting mentally undressed right now.”  
“Jess..”  
Jess watched Rory giggle at his embarrassment,”What are you up to right now?” he asked her.  
“Me? Just enjoying the show.”  
“Funny.”  
“But really, nothing, wanna get out of here?”  
“Sure. Bookstore?”  
She nodded and got up, taking a cup of coffee to go. As they walked out Rory giggled again.  
“What’s so funny?” He asked giving her a stern look.  
“Its fun to see you get so flustered,” she teased at him while looking at Babette and Miss Patty who were watching them through the window.  
“I’m not flustered,” he answered back,”just..annoyed.”  
“Uh huh. Well I mean you are a plate and a half after all,” she smiled at him.  
“Geez,” he growled back while walking towards the bookstore.  
They spent a couple of hours going through each aisle and seating next to each other while reading what they picked out. Jess was still able to read through a book in less than 10 minutes but that didn’t stop him from buying a decent stack, he always went back and read them through multiple times. They reached the register and buy their haul, at least 10 each. A couple of giggling teenagers looked over at jess from the corner, whispering to each other. Jess rolled his eyes and walked out with Rory.  
“So you’re going to ignore your fan club?” Rory said holding in her laugh.  
“Stop,” he said back with irritation,”are there no teenage boys for them to fawn over?”  
“Sure there are, but you’re older, have a beard, wear a jacket that doesn’t have a skull logo on it, truly a list of endless qualities.”  
“This town just gets more charming each time I come back..”  
“You miss it, don’t lie,” Rory teased.  
“Oh yeah, I miss the black sheep, I was really getting used to being ostracized,” he deadpanned back.  
“I knew it.”  
They walked over to the Gilmores’ household which always made Jess nervous, remembering the days of sneaking into Rory’s window and being under the scrutinizing eyes of Lorelai. As Rory opened the door and they stepped in, the house was a mess of boxes and a disarray of junk thrown everywhere.  
“Mom?” Rory said with confusion trying to zig-zag in the small pathways of floor that was left.  
There was no answer, they headed upstairs, careful not to topple over piles of indiscernible clutter.  
“Mom!” Rory called out in the hallway that was almost too crowded to get into any room.  
“In here!” said a muffled Lorelai from somewhere.  
“Where!” she called back. Jess followed in similar confusion, the scene looked a lot like Luke’s apartment did last week when he arrived.  
They heard a crash of various unknown items and muttered curses from Lorelai as she came out from her room to the hallway to meet them.  
“Hi!” she said nonchalantly.  
“Mom…What’s going on?!” Rory asked in irritation.  
“Nothing! Its all totally fine. Completely handled.  
Jess and Rory stared at her with concern.  
“Okay. Its not fine. I’m freaking out! Why do I own so much shit? When did I become a hoarder Rory? How did you live in this house? Its insane that they let me keep you and you weren’t taken away by the feds. How is Luke going to live here? Where is Paul Anka!” She was pacing in the small clear trail in front of them.  
“Well I had a wardrobe to escape to when the hoarding got bad but..” Jess smirked and held back a laugh. He knew that Lorelai was only scared about her upcoming wedding even though Luke and her have been together for years, he’s assuming the pressure is something that happens to everyone who gets married.  
“Oh my god!”  
“Mom. I’m kidding. You’re not a hoarder. I mean I admit having five different versions of Cats the musical on VHS is a little frivolous..especially since you don’t really like musicals, but I’m fine. I don’t think I’ve inherited any unibomber tendencies.”  
“I needed to hear how Cats sounded in German!”  
“Luke did this last week,” Jess interjected hoping to lull the insanity in front of him.  
“What?” Lorelai said while looking through a pile of clothes in front of her.  
“Luke pretty much gutted his apartment, when I got there I couldn’t open the door. He had I think five singing fishes, you know those ones that are fake and mounted and you get off the infomercials. Anyway, you both are getting cold feet. Its normal…or so I’ve read? Either way, you’ve been together for a long time and obviously have had a bond for longer than that so there isn’t really anything to worry about. I’m sure Luke wouldn’t care if you owned five copies of Cats the musical. Do you need help cleaning all this or is this your new life now?” Rory and Lorelai were staring at him in dismay, he had ranted which wasn’t a usual occurrence for him.  
“What?” he asked wishing to break eye contact with them.  
“Wow.” Rory and Lorelai answered in unison.  
“Thanks Jess,” Lorelai added smiling at him.  
“Um. No problem..” he said turning away and beginning to shift through the hallway’s mess.  
“I’ll take the kitchen,” Rory said going downstairs.  
They spent the rest of the day cleaning up the house and sorting through what Lorelai didn’t need versus what she wanted to keep. In the end, a lot did end up being removed, including the five copies of Cats. It was late evening when they finally finished, they ordered a couple of large pizzas and sat in the newly organized living room that didn’t look much different than it did in the first place.  
“I think I’m finally getting back from the void,” Lorelai said while biting into her sixth piece of pizza.  
“I’m surprised you can feel anything after eating that much pizza in 10 minutes,” Jess said opting for a salad on the side of his slices.  
“Ha its like you don’t know our eating habits or something,” Rory replied, also indulging in her sixth slice.  
“No, I know it well, doesn’t make it okay,” he laughed.  
Rory scoffed back at him while Lorelai smiled looking at them both. Jess gave her a questioning look which she shrugged off, he was trying not to be painfully obvious, but nothing could be hidden from Lorelai especially if it involved her daughter.  
—————————————  
The next day was the wedding, Jess woke up at the Gilmores’ house, he forgot he fell asleep on the couch with Rory. His arm was around her and her head was on his shoulder, he creaked his neck as this was the most uncomfortable position to fall asleep in. He loosened his arm slowly, not wanting to wake her just yet. It was 6am which was too early for any Gilmore to be awake. He laid her on the couch, placing their blanket over her, sure that Lorelai had placed it on them during the night. He walked through the kitchen to the back porch, taking out a smoke. There was Luke reading the paper and drinking a cup of coffee, he wasn’t sure when he came home last night or when he had woken up, but he was sure that he saw Rory and him asleep together.  
“Morning,” he said not looking up from his paper.  
Jess lit his cigarette and took a long needed drag, he hadn’t smoked the last couple of days since spending time in with Rory, the familiar sting to his lungs was definitely needed.  
“You’re up early,” Luke added as Jess sat down on the bench next to him.  
“I always wake up at this time. Have since high school. Did you want me to stop by the diner?”  
“No need, Cesar’s got it. It is my wedding day after all.”  
“It is. How ya feeling? Missing those singing fish?”  
“I’m ready,” Luke smiled out into the backyard, Jess could tell he was genuinely happy.  
They spent some time together outside in silence, admiring the rising sun and frost on the leaves.  
“Think I’m gonna get a haircut,” Jess said wringing his hands through his hair.  
“Oh yeah? You don’t have to. For the wedding I mean,” Luke answered.  
Jess smirked,”Glad you aren’t too conservative. I’m kinda just ready for a change..”  
“Change is good. Well, you can go to my guy, he’s right around the corner from the diner, ask for Al.”  
“Like Al’s Pancake World Al?”  
“That’s the one.”  
“Of course.”  
Jess’ hair was the shortest its been in years, looking akin to his high school days but with less gel, mousse, etc. He decided to keep the beard, trimming it slightly. He brought his own suit since the one tailor in town was a 80 year old woman who, though extremely talented, took months to get back to anyone. He put aside his ensemble for now, going downstairs into the diner to see if he could help out Cesar or find his uncle.  
He walked downstairs and opened the curtain, going behind the counter. He looked up and realized that everyone had gone silent and were looking at him.  
“Whoa,” he heard Babette say from the corner.  
Rory was at the counter, looking at him from her cup.  
He looked at her,”…what?”  
“Your haircut..”  
“What about it?”  
“It looks…really good,” she answered, blushing slightly and looking away.  
“Oh. Uh thanks..” he said awkwardly also blushing.  
He took a couple of orders from Cesar, giving them to each customer, women going silent as he filled their coffees throwing him a smile. He felt like a spectacle again.  
“So um do we need to get the towns’ square ready for the evening?” Jess asked Rory sitting next to her, her body instantly tensed at his presence. He smirked a little at his accomplishment, she had begun to tense up more around him over the last week; he wasn’t sure if it was him, the wedding, or that she was leaving tomorrow.  
“Oh yeah! That’s why I came here, I was hoping you could help me coordinate some things, hang some lights, do the heavy lifting if possible. My grandparents are in town so my mom’s a little preoccupied with that.”  
“Ah the grandparents,” he reminisced the last time he saw Emily Gilmore, he wore a black eye and left a hardy impression on her. Knowing what Rory has told him about her grandparents, it was unlikely she had forgotten it.  
“Yup. Luckily, they’ve actually been really great about this since its actually happening and Luke seems to get along..enough with them anyway.”  
“I’ll be sure to steer clear of Luke till later. Can’t really imagine all he’s dealing with right now.”  
“He’s doing surprisingly well. They both are. I think they just needed each other for mutual insanity.”  
“Sounds about right,” he smiled, he was happy for his uncle. If anyone deserved love and stability, it was definitely him.  
“Lets go. I’m sure you’re over being looking at from a magnifying glass,” Rory giggled.  
“Please.”  
They stepped outside into a cold afternoon, it was the first days of February and snow was still in the forecast but strangely nonexistent today. The usual townspeople were out but everyone was involved in the preparation for tonight; just how Lorelai and Luke wanted it. They joined everyone else in setting up chairs, tables, lights, and flowers. It was dusk by the time they had finished and it was time for Rory and Jess to get themselves ready for the night to come. Rory made her way to her house as Jess departed back to the apartment.  
He cleaned up, slightly moussing his hair enough for it to withhold its volume, changing into his charcoal grey suit with a white button up, and black tie. He still kept his boots on for good measure. He walked over to the towns’ square where the majority of the town was already seated. He found Liz, TJ, and Doula all heading over to sit down and talked to them a bit before getting distracted by Rory coming up from the distance with her grandparents. She gave him a shy wave as they passed each other. They all took their places, Rory and Jess seating next to each other since they were the man and maid of honor.  
“You look amazing,” he whispered into her ear. She was wearing a light pink dress that laid right above her knees, it had a strapless upper bodice to its tulle bottom, though she had to wear a coat over it Jess couldn’t help but stare with her long dark hair draped over her shoulders, she looked like a dream.  
She smiled and placed her hand on his arm,”so do you.”  
There ceremony started, as they all stood up Jess watched as Luke came to the front. Kirk behind him, as in Stars Hollow fashion, he was the only person in town who was ordained to marry people. Everyone turned as Lorelai walked down the aisle; her long ivory lace dress trailing behind her. Luke’s eyes teared up as everyone else’s did in the audience. As they took their vows, Jess looked to Emily and Richard Gilmore who were sobbing. Rory took Jess’ hand as she watched, wiping away tears from her cheeks. He caressed her fingers lightly.  
After the wedding, the seats were moved around for the dance floor and tables set up for the massive amounts of food that Sookie had prepared, she brought her guns blazing. The bride and groom danced slowly to their first song as Jess watched Rory from across the floor. As the Jesus and Mary Chain came on, he walked to her, offering his hand. She took her and smiled.  
“Huh, didn’t peg you for a dancer.”  
“I’m not, but it is tradition.”  
“And when you think tradition, you think Jess Mariano.”  
He smiled and looked at her face, taking in all its perfection, including the small creases around Rory’s eyes that have developed over the years, the only hint of her becoming older. The string lights made her skin a warm glow. He relaxed as she put her arms around his shoulders.  
“You’re good at this.”  
He placed his hands around her waist. They were so close, he wanted so badly to be able to kiss her right there. Soon enough, the song ended and they departed from one another slowly taking their places across the floor. He watched as Emily Gilmore smiled and whispered something to Rory while looking at him, she smiled in response.  
As the reception went on, Jess decided to take a walk to clear his head. The ceremony was beautiful but he couldn’t help but feel overwhelmed. He took a cigarette out of his pocket and leaned over the bridge staring into the frozen lake below.  
“I thought you’d be here,” Rory appeared her arms wrapped around holding her jacket in place.  
“No fooling you,” he said in response without looking at her.  
“Are you doing okay? It started feeling a little crazy back there.”  
“Yeah I’m fine, just needed a little air.”  
“Oh sorry, I shouldn’t have assumed..”  
“You can stay. Not opposed to your company.”  
They leaned next to each other, both staring into the same reflection of light below.  
“I’m nervous,” Rory said lightly.  
“Why?” Jess asked in the same tone.  
“For leaving. Its so long. I’m going to be alone.”  
“Its not super long. Plus I’m sure you’ll have your mom calling everyday. You won’t be alone.”  
“You won’t be there.”  
He turned to her,”I know.” He could feel his heart beating that familiar sound in his ears again, but this time his body ached as he looked at her.  
“Will you miss me?” she said turning to him.  
“Always.” Rory slowly reached out and grabbed his jacket pulling him forward towards her.  
Jess closed the gap and gave Rory a gentle kiss first, unsure if he should proceed. Before he could think twice she pulled him in closer deepening their kiss as she moved her hand from his jacket to his neck. He felt her tongue at his lip asking for entrance as he met hers with his. She groaned into his mouth which propelled him to tighten his grip on her waist, pinning her against his body. Years of tension came up as they rubbed at each other’s necks, intertwined their fingers in each other’s hair.  
“Rory! Where are you!” Lorelai called from nearby.  
They stopped and broke apart slowly, catching their breath with their foreheads against one another’s.  
“Don’t leave,” Jess whispered. He didn’t want to break this moment, he didn’t want to not have her for another six months.  
They kissed again, softer this time. She rubbed his face, touching his lips with her thumb.  
“See you soon, Dodger,” she said as she broke away one last time with a smile walking away into the night.  
Jess sighed looking after her. He turned back to the lake, bringing out the cigarette he desperately needed.


	6. Runaway

**Summary for the Chapter:**

> Jess gets a hold of his life while Rory is gone, but what about when she comes back?  
> Literati love was never easy and old habits die hard.

The morning after Rory was gone as expected, leaving quietly and discreetly, she left a note on Jess’ windshield with the various addresses she’d be staying at. He thought about the night before the entire drive back to the city, feeling her phantom kiss on his lips. The first three months were easy for him to get through, he spent most of his nights writing into the next days and his days he spent completely reorganizing the shop. He started a zine collective to mirror the one in Philly and eventually all the work he put himself into got the attention from various local papers and even agencies were interested in taking him on. It was around the third month that his writer’s block hit, the worst he had ever experienced. He couldn’t get through one more page of his book without erasing the entire thing multiple times. This was also around the time that he lost contact with Rory, he decided not to dwell on it blaming it on coincidence instead of causation. He needed to get out of the city, try another environment in hopes of sparking some motivation so he decided to move back to Philly temporarily managing Truncheon’s headquarters; Matt took over the New York location until he decided to come back and Freddy had no qualms with his leaving since he literally did all the work they needed to do.

“So you haven’t talked to Rory lately?” Chris asked during his first week of being back in Philly.  
“No,” Jess asked looking over his editing.  
“So you ran off back to Philly to distract yourself?”  
“You could say that.”  
“What about your therapy?”  
“I’m still calling him every week.”  
“What about the shop?”  
“Freddy’s cool with it.”  
“What about-“  
“Chris. I came here to try to relax and be less tense, I’d really appreciate if you could give me space because I feel like punching you right now.”  
“Fair enough! I’ll be downstairs boss,” he said while walking out of the office. Chris had a habit of borderline harassing Jess whenever possible, but he knew he had good intentions regardless if he wanted to punch him every time.  
It was late May and already feeling like summer; it was hot and starting to get muggy, two things that made Jess and the rest of Philly irritated, but regardless he ventured out to the parks by Truncheon to spend time writing in the sun with headphones in, a daily part of his routine. He started to concentrate when he felt his phone vibrate, as if by some sort of sign from the parallel universe his life had become over the last year.  
Met a wannabe version of you I had to interview today. He even liked Hemmingway!  
He smirked, glad Rory was still able to think of him.  
There can only be one.  
He texted back as she called him.  
“Hi,” he said as he answered her call.  
“Hi!” she exclaimed back.  
“I’m guessing you killed my doppelgänger?”  
“Oh yeah, he’s obsolete, don’t worry about it.”  
He smiled, she was goofy, it always made him instantly feel comfortable.  
“So how’s it been?”  
“Its been great, the west coast is totally different, everyone is pretty much retired even the young people. Weirdly laid-back. Its nice, but I miss it over there.”  
“Yeah I don’t think I could deal with laid-back, I rather someone be yelling in my face every couple of blocks. Been there, done that.”  
“Right! God, its almost like they enjoy their lives out here.”  
“Mind-blowing.”  
They spent over an hour catching up, it was as if they didn’t go weeks without contact. He still felt his heart race whenever they talked, it became worse with each phone call. He missed her but he wouldn’t admit it since he didn’t want to ruin her travels, he only hoped she missed him too.  
“How’s it been over there? Almost done with the greatest american novel?” she asked genuinely.  
He laughed,”wouldn’t say its even okay at this point. Have a bit of writer’s blocks. Hoping it will just kick in…eventually. How has your writing been?” he wasn’t the most comfortable talking about his writing, even during interviews he’s had in the past with each book he’s written he never liked to reveal too much about that side of him. Writing was not only personal, it was a part of him that would open up every time he brought his pen to paper.  
“Not the best either honestly. Maybe we’re mentally sending blocks to each other..”  
Jess laughed,”oh yeah? You tryin’ to sabotage me Gilmore?”  
“Yup, it was my plan all along.”  
“Damn, you’re sneaky.”  
When they hung up, Jess sighed, feeling relaxed and tense at the same time. He put his headphones back in and was finally able to write.  
————————————————  
Jess spent two weeks holed up between Truncheon or the park down the street, nearing the end of his book. He kept Chris’ advancements for going out to various events at bay, he truly was trying to finish and meet his personal deadline.  
“C’mon, its a good lineup.”  
“Thats what you said over the weekend.”  
“Yeah and?”  
“Chris..”  
“C’mon Jess! You’ve really been pent up here, its a bit concerning for me considering half the time I don’t know if you’ve even left your room each day.”  
“You just need a wingman.”  
“I mean, sure, but you’re not a very good one anyway since literally everyone finds you attractive, even me!”  
“Geez.”  
“So you’re coming?”  
“Will this one time make you shut the fuck up for the rest of the week?”  
“Yes. Probably.”  
“Jesus. Fine.”  
They headed to the bar, which Jess was already regretting as they hopped on a crowded extremely stuffy train during commuting hours. He was so used to being cooped up it was a little overwhelming, Chris had agreed to buy him all his drinks for the night which he planned on taking full advantage of. He ordered a shot with a whiskey on the rocks immediately after, he figured he was out so he might as well attempt to enjoy it.  
They walked towards the table and thats when he saw her. She looked up at the same time he spotted her and they locked eyes. Marie had an electricity to her that he was always drawn to; she waved him over which he felt awkward about since Chris was with him.  
“Uh Marie’s here..”  
“Yeah, I know.”  
“Wait..you knew what?”  
“That she would be here.”  
“So you invited me to this and knew she would be here.”  
“Well for one, she listens to the same music we do, two if you had a facebook you would’ve already known that.”  
Jess clenched his jaw, restraining himself from what he really wanted to say to him. They walked over and sat with Marie and another woman he didn’t recognize.  
“Didn’t know you were going to be in town.”  
“Yeah. Kinda a last minute idea.”  
“How long you staying this time?”  
“Awhile.”  
They looked at each other and Jess could see Marie’s eyes trail to his mouth. He clenched his jaw again and took a sip of his drink. Luckily the music started so they were able to at least have some space between them. She stood in front of him, rubbing against him every once in awhile when the crowd would shift. He looked over at Chris for some sanity, but found him talking up Marie’s friend with no attention to what was happening. Jess wasn’t opposed to being around Marie, even preferring her to the other women he’s seen over the past couple of months, but he did have feelings for her before and felt strange now that Rory wasn’t here between them.  
He stepped out for some air after the band finished, which he seemed to have to do a lot of lately. He was about to light a cigarette when Marie stepped out.  
“Hi,” she said shyly.  
“Hi,” he said not looking at her but concentrating on his cigarette.  
“So..you’ve been holed up at Truncheon this whole time or what?”  
She knew him well regardless of how much he tried to hide from her.  
“You could say that.”  
“Would’ve been nice to know you were here.”  
“I’ve just been under the radar, sorry.”  
“Its okay. I’m glad you’re here now.”  
She moved closer to him and took his cigarette, putting it in his pocket as she pulled him to her, he moved his hand under her shirt over her hips, his other arm around her waist as he kissed her, they pushed themselves against each other and deepened their kiss. He thought to himself how soft he’s gotten but also how he didn’t really try too hard to stop this from happening. He felt lonely despite trying to convince himself otherwise and he was trying not to wait for Rory while she was gone; he went through a list of excuses that made him feel like his motives were justifiable.  
—————————————————  
He dressed in the morning, lacing up his boots as Marie sat up in bed still naked next to him.  
“You know you could stay a little longer,” she said moving behind him, kissing his ear. He paused hitching his breath.  
“Can’t. Got to get this writing done.”  
“Huh. Okay,” she pouted at him. He kissed her, there was a part of him that wondered if they had anything beyond just being friends with benefits but he enjoyed what they had now; casual and wild.  
“You’re really hooked aren’t you?”  
“What?”  
“You’re in love with her. I know you.”  
He looked at her, biting his lip he smirked,”I’m not talking about this with you.”  
“Didn’t think so, but its okay you know,” she had a tinge of hurt on her face, he was beginning to feel guilty that he ran into her in the first place.  
“I’ll see you later,” he said as he walked out her bedroom door.

He hated how transparent his feelings for Rory were; he wondered if she caught on to how intense they’ve become over the last couple of months or she was really trying to remain casual with him. He tried to push these thoughts aside as he reminisced on the wedding, their kiss, his body feeling like it was on fire whenever he was close to her. He sat down and wrote for hours in the park until the sun went down and he could feel the heaviness that was on his chest subside.  
—————————————————  
It was July and Jess managed to get his book completely done, he was almost ready to publish it but needed a fresh set of eyes to edit it, he emailed it over to Rory in hopes that she had enough time to help him out.  
It was her birthday and he attempted to call her twice that day to wish her a happy one, but it went straight to voicemail each time. She was nearing the end of her travels and apologized profusely each time she didn’t talk to him for weeks at a time. Jess saw a picture of her with Oliver and Laura in an article introducing their collaborative journalism, he hated seeing her next to him with his hand on the small of her back; he tried to push his jealousy aside as he closed the window on his laptop. He broke things off with Marie at the beginning of the month, he was quite busy himself, though she knew that wasn’t the reason why.

Jess left back to New York to get ready for his publishing party, he thought of staying in Philly longer, but it served its purpose as a safe haven away from home.  
“I think I wanna move out here officially,” Matt said as Jess got home.  
“Oh yeah? a less cynical version of Philly would suit you,” Jess replied putting down his duffel bag.  
“Is Rory coming tonight?” Matt asked while cleaning making some coffee.  
“Uh not sure. We haven’t talked in a minute.”  
Matt looked at him while sipping from his cup slowly.  
“What?” Jess asked, not wanting to deal with another third degree from one of his best friends.  
“Are ya’ll cool? I mean, has this time apart made clarity for you at all or maybe..its your publishing party and she helped you edit your book. Thats kind of a big deal don’t you think.”  
“I don’t know. We’re both busy and I’m not trying to hold anything against her. If she can make it cool if not, I’m trying not to focus on it.”  
“Right..but you are though.”  
“Matt..” Jess gave him a glare.  
“Dropping it. Got it.”  
They sat together drinking coffee and catching up before heading to Truncheon to get everything ready. Matt was the most rational of the three of them, his chill demeanor made him a great business partner and an even better friend. Over the years, Jess often went to him for advice or a mediator when Chris and him would butt heads. Jess didn’t have a lot of people in his life that he counted as more than just acquaintances, he’s glad in his adult life he was able to find meaningful friendships.  
They walked their way over to Truncheon as Jess’ phone vibrated.  
Won’t be able to make it tonight, still trapped in LA. I’m so so sooo sorry, I’ll make it up to you :(  
Seeing the text definitely disappointed him, if there was one person he wanted to be there, it was Rory.  
I get it. Hopefully see you soon.  
He wasn’t sure what else to say, but tried to hide his visible mood when walking into the building. There was already a good crowd of people; mostly just current writers, employees, and friends of friends, but Jess brought out his flask of whiskey nonetheless to attempt to calm his nerves. He found Chris and Matt upstairs talking to Luke and Lorelai who surprised him.  
“Didn’t know you’d be here,” he said while giving them a hug.  
“Didn’t know you gave hugs,” Lorelai smiled back.  
“Touche.”  
“This is great Jess! Really has that starving artist vibe, but cleaner,” Lorelai said while walking around the room.  
“Uh thanks I guess. Did you want a drink? There’s always some sort of mixed whatever at these things.”  
“Sure. A beer would be great,” Luke answered, he was always awkward at these events.  
He got them some beers and they sat down together,”are these things always so crowded? this is nuts.” Lorelai said sipping her beer and eating peanuts from a bag in her purse. Jess and Luke both gave her a questioning look,”What?”  
“Nothing. They’re generally not too packed, usually its just friends of friends or of my coworkers.”  
“This is amazing, don’t be humble for the one time you shouldn’t be humble,” Luke said nudging him.  
Jess smiled, unsure if he’ll ever get used to being praised instead of punished over his accomplishments.  
It wasn’t long before it was time for Jess to read excerpts from his new book Major, Minor which was always his least favorite part.  
He entered the reading room which was packed to each corner, his nerves were getting the best of him but he could make this as quick as he needed to.  
“Hey everyone, I’m Jess Mariano, uh owner of this building I suppose. Going to read a bit from my new short novel Major, Minor. I’ll make this as quick and painless as possible.” The crowd smiled and Jess could see Luke in the front row with Lorelai, they were both smiling and he thought he almost saw a tear in Luke’s eye.  
He began and thats when he saw her walk in, she was hard to miss wearing a long red sundress her hair still cascading down to her hip. He paused for a second which was fine since it made sense with what he was reading and she smiled at him.  
The crowd applauded as he finished and left the small podium up front. Lorelai wooted from the front row as he laughed and nodded his head. She gave him another hug as Rory came forward.  
“Just as amazing as when I was editing it,” she said as she gave him a tight hug.  
“Trapped in LA huh?” Jess smirked at her. “You two knew about this didn’t you?” he turned to Luke and Lorelai.  
“Nope. Not a clue,” Luke deadpanned. Jess glared at him,”it was all her idea!”  
“What a snitch!” Lorelai exclaimed.  
Jess’ heart jumped as Rory lightly touched his hand with hers. He was thankful for his ability to completely neutralize his facial expressions in time of need.  
They changed their course of action, instead having dinner together before going to the bar down the street. Jess wasn’t sure he was ready for Luke and Lorelai to see him incredibly drunk and singing David Bowie just yet.  
They picked a small diner nearby, since Rory and Lorelai were not up for the amount of vegetables that thai food included.  
“How are you still eating a salad when there is literally a gigantic menu filled with fried goods?” Lorelai asked Jess looking horrified.  
“I didn’t think fried ice cream sounded appetizing right now. I haven’t drank enough to allow that to happen. I don’t think I’ll ever drink enough for that,” he answered honestly.  
“God you are your uncle’s nephew.”  
Jess rolled his eyes turning to Rory,”so when’d you get back?”  
“Technically yesterday night, but I went straight to Stars Hollow and got sucked into a double feature..”  
“Um there was no peer pressure okay, you’re the one who wanted to be nice to Kirk!” Lorelai exclaimed.  
“So the double feature was basically two films made by Kirk’s new smartphone and it was about four hours long.”  
“Yikes. Sounds like you were invested.”  
“Very. I felt like it really showed us a side of Kirk we weren’t really sure we wanted to know in the first place. Lots of things we probably can’t unsee but that was guaranteed.”  
“Say no more.” Their knees were touching under the table and Jess wondered if Rory felt a lump in her throat too.  
“Well we should head out if we want to catch the town meeting,” Lorelai said with thick sarcasm.  
“Right,” Luke said giving her a raised eyebrow.  
“Sad we won’t get to witness you singing Thin Lizzy, I can hardly imagine you even listening to that band let alone head banging to them,” Jess glared at Rory as if she gave up his biggest secret.  
“What? I said nothing!” Rory exclaimed. Jess hardened his glare,”Okay! I admit it! I showed her the video okay!”  
“Is nothing sacred? Like a man enjoying a dad thrash band and drunkenly choosing them for karaoke?” he shook his head.  
They gave their goodbyes and hugs to Luke and Lorelai before they were off to O’Miley’s. Walking in silence for awhile Rory turned to Jess and looked at her while she looked ahead.  
“So..how have you been?” she asked awkwardly, Jess was wrapped up in his own head feeling increasingly uncomfortable as he realized they were walking alone together.  
“Good,” is all he could muster, he kicked himself why can’t I talk to her now.  
“Good,” she countered.  
“Hey, are you okay?” Rory asked looking over at him after a long pause.  
“Yeah. Just didn’t expect you home is all.” He was nervous, he felt similar about ten years ago when he first started getting to know Rory.  
“I’m sneaky remember?”  
“Just a regular snake in the grass,” he smiled at her as she pushed him.  
“Hey!”  
They arrived at O’Miley’s as the crowd applauded and cheered as Jess walked in. It was 10pm but somehow everyone was already ten levels ahead of them in toxicity. Matt pulled Jess and Rory to the bar, immediately buying them shots before even saying a hello.  
“This is huge, bigger than your other parties!” Rory exclaimed over the loud cover of Sioux and the Banshees Lane was doing.  
“Seems about the same to me. Same obnoxious amount of people getting wasted.”  
“No way, they’re all here for you. Admit it, you love it,” Rory said while interlocking their arms together.  
“Yeah I’m internally cheering for it,” he deadpanned taking another shot.  
They sat with their usual crew of people as Lane came back from the stage giving them a hug and taking her seat next to Dave. Matt and Chris were arguing over which Robocop sequel was better and eventually moving onto whether Predators or Alien vs. Predator was better. Jess watched as they became heated, Chris absent-mindedly spilling his beer on the table as he gestured his distaste for the Predator franchise. He smiled, missing these moments. Rory didn’t unlock her arm from him even as they sat down and he was comforted by the warmth of her body against his.  
They opened up a bit, talking amongst themselves over what each other had missed over the last month of their lack of communication. Rory had written over 10 long-winded interviews with various independent writers and told stories of Laura getting exceedingly drunk and sleeping with Jess’ doppelgänger. She briefly mentioned Oliver and his lack of knowledge on the beats movement which sent a writer in Oregon to walk out on him. Jess couldn’t help but laugh at that.  
“Not everyone is as knowledgable as you are, Bukowski.”  
“Please. Its high school literature at this point. If you haven’t read Ham on Rye before the age of 18 how are you planning a career as a journalist?”  
“Green doesn’t look good on you. And neither does sass.”  
“I have no idea what you’re talking about. Just presenting facts here.”  
“Uh huh.”  
“I mean he had to hangout with you for 6 months. Sounds like a burden to me.”  
“Rude!”  
Lots of cocktails and beer went around the table, enough for Rory to get up to the mic and sing the Smiths and Matt to rip off his shirt to Bruce Springsteen. The bar was sweaty and hot, summers in New York were no joke as each day rose in the 90s and the night air hung with humidity. He stepped outside to breathe and smoke a cigarette which he hasn’t done in weeks.  
Rory stumbled out, always having the best timing.  
“Hi,” she said leaning next to him.  
“Hi,” he said back putting his cigarette back in his pocket.  
“Sorry, didn’t mean to interrupt your alone time. Its just crazy in there. Did you see Matt crowd surfing?!”  
“Sorry to have missed that. Just wanted some air even though it doesn’t feel much better out here.”  
“You were happy earlier, what happened?”  
“Nothing. Who says I’m not happy now?”  
“Your frown.”  
“Thats just my face,” he answered sarcastically. Throughout the night Jess couldn’t help but think about them and how confusing it all was. He figured the alcohol would help numb his anxiety, but it only served to make it worse.  
“Does this help?” she said as she grabbed his hand.  
“A bit,” he turned to her.  
“Okay. What about this?” she asked putting her hand to his face and leaning into him. Chris and Matt walked out, or rather fell out, of the crowded bar’s entrance as Rory and Jess jumped away from each other. They were both drunk enough that they didn’t realize what was happening and instead said incoherent gibberish about them sleeping at Truncheon or something and seeing him in the morning.  
Jess bit his lip and exhaled,”I should probably follow suit, make sure they don’t follow Pennywise into a gutter along the way. You okay to get home?”  
“Oh okay. Yeah. See you tomorrow?” he thought he saw a look of disappointment on her face. They were both drunk and his hazy mind was trying to make the right choice.  
“Sounds good,” he answered while walking away.  
“Oh and welcome back Rory,” he turned and smiled at her.  
“Bye Jess,” she smiled back at him.  
————————————————  
Jess woke up with a huge hangover the next day, usually he was able to avoid one, but he remembered he had mixed quote a bit of hard liquor with rounds of beer and how he managed to not puke and remember all of it was beyond him. It was 8a, early enough for him to roll over and sleep for a couple more hours but his apartment was already hot and he couldn’t stand staying in bed any longer. He knew Rory well enough that she wouldn’t be up for awhile, so he exercised and cleaned up his apartment which didn’t need much organizing in the first place. He was nervous to have her over, especially in close proximity to his bed as his urge to give into his feelings for her have only grown over their absence even if he tried his best to repress them.  
He managed to eat a healthy amount of bread for lunch, his stomach not letting him indulge in anything too rich.  
I’m so hungover, but lets go to the museum!  
Rory texted around noon, as Jess figured.  
Pretty vague considering the amount of museums in this city. Do you mean all of them or ?  
The Morgan duh! The only one that matters considering its a library at the same time.  
Ah my bad, should’ve guessed that.  
I’m on my way over!  
Jess hopped in the shower and forced himself to wear a pair of shorts. He tried his best to only wear jeans and tshirts throughout the heat, he wasn’t much for summer wear but it was going to be in the mid 90s+ and the idea of being out in that was enough for him to change. He had achieved a dark tan which he forgot he could get easily due to his Italian and Spanish heritage, but every summer he surprised himself considering he avoided the sun as much as possible.

Rory arrived in high-waisted shorts and a cropped off the shoulder shirt. She could really wear anything and look amazing, but the amount of skin she was showing was difficult for Jess not to look over at her smooth milky legs and the mid-riff that would occasionally peak out when she would bend.  
“Your place looks great, I mean it looks exactly the same as when I last saw it, but clean. My place is a mess in comparison. Maybe you can help me organize,” she gleamed at him while looking at his book shelf.  
“Trying to get me to move large furniture up your staircase again? You’re gonna have to pay me this time.”  
“More like keep me from becoming a hoarder, I brought back a lot of stuff from the west coast. Mostly shit, like why do I need a Isaac Asimov magazine from the 70s? I don’t. Oh, I brought you something by the way,” she opened her tote bag and handed him a book.  
“Old Man and the Sea? whoa, is this a first printing?!” Jess exclaimed while holding the delicate used book in his hand. It smelled of every bookstore it had belonged to, the pages dog-eared and stained which were his favorite parts about secondhand copies.  
“Yup. I found it in this small town, really Twin Peaks town actually, had the smallest bookstore with the most valuable books that cost practically nothing. The coffee was amazing too, you’ll have to see it for yourself one day.”  
“Did you have five unicorn figurine stores like Stars Hollow? I want that level of kitchyness in my small towns.”  
“We have eight now actually! pfft, thinking we’re a five unicorn figurine kind of town, please.”  
“Guess I haven’t visited in awhile. Thanks Rory, this is fucking cool,” he said while still examining the copy in his hand, admiring the soft edges and worn in spine.  
“Of course. I was pretty much obligated to get it, I don’t think I could’ve kept this from you.”  
“Glad you thought of me while you were away.”  
She gave him a small shy smile,”are you ready to go see more old books?”

They walked out onto the sweltering sidewalk, somehow his apartment was much cooler than the outside world.  
“Jesus, I’m glad we’re going to be inside,” he said glaring up into the sky with his hand above his brow shielding himself from the sun.  
“Its not too bad, I like the heat. Sometimes.”  
“Geez, who are you?” he teased her as they walked towards the subway together.  
“I’m a Californian now, I forgot to tell you!”  
The museum was a short walk from the Grand Central station, but each block Jess felt like he was getting more and more irritated, facing a mild migraine that struck him right behind the temple. Rory gave him some advil which he figured was a thing that a organized woman like Rory would do. He remembered when he was sick as a child and how his mom would leave him with a liter of 7-up and let him fend for himself as he laid in bed with a 101 fever.  
They spent hours looking through each section of the library and taking the Emily Dickinson tour/lecture. Poetry wasn’t always Rory’s cup of tea, but Jess liked to think he had a bit of influence on Rory’s literary choices. After the lecture, they stopped by a hot dog cart and walked to a nearby park to find some shade. Jess propped himself on a tree while Rory laid with her head on her purse near his lap. He wished he could reach out and brush her hair out of her face. Spending the day with her didn’t make his confusion any more clarified.  
“Why did your last relationship end?” Rory asked after they delved into their books.  
Jess paused,”Well she moved away for a job. To Washington. We tried long distance for awhile, but it got messy, didn’t work for her so..she moved on with someone else.”  
“I’m sorry..didn’t mean to bring up anything,” Rory said looking at him with sympathy.  
“Its fine. It was over a year ago, it was a good experience overall.”  
Rory sat up to look up at him,”Was that the girl you talked to at O’Miley’s?”  
“What girl?” he wasn’t entirely sure who she could be talking about since he didn’t remember talking to anyone last night.  
“It was when I first started hanging out with you again. She was really pretty, long dark hair, seemed pretty close to you..”  
Jess could hear the tinge of jealousy in her voice,”Oh that was Marie. Not an ex, just someone I used to hang with.”  
“Oh..,”Rory looked away from him as Jess smirked.  
“What about you? hard to believe that the blonde dick from Yale was the last person you decided to date,” Jess laughed as Rory pinched his arm.  
“No, not the last guy, I guess the last serious relationship. But when someone proposes to you and you prioritize your career over them, it kinda puts a damper on romance..”  
“He proposed to you!?”  
“I thought Luke would’ve told you that by now. Yeah..he proposed and wanted us to move away together, but I really wasn’t ready for that. Or..at least not with him at that time,” she was fiddling with her hands in her lap, trying to avoid embarrassment.  
“Do you regret it at all?”  
“I did at first. I missed him, but then I realized our relationship was kind of bullshit and I was glad to finally be out of it.”  
Jess laughed feeling a sense of relief, remembering that night back in Philly when Rory’s words cut into him. She leaned her head against his shoulder as he went back to his book. They’ve opened up to each other over the last year, even if distance had temporarily gotten in the way, they were always able to get back to one another.  
“Wait, I need to go, I can’t get comfortable!” Rory said suddenly getting up.  
“What’s wrong?” Jess asked, rising to her, feeling that familiar pang in his stomach return hoping this wasn’t a mistake.  
“Nothing’s wrong, I just forgot I was supposed to meet with Lane in..great half an hour! I have to help her decorate for Dave’s birthday tonight!” she quickly packed her bag and began walking onto the grassy knoll. Jess followed just behind her.  
“Isn’t it just at some bar? I didn’t think there would be party favors and batman piñatas involved.”  
“Its at a bar that Lane reserved, she’s inviting basically everyone they ever met and there will in fact be a piñata involved.”  
Jess cringed, not a big fan of birthdays in general, let alone ones involving grown men hitting a piñata.  
“Don’t make that face, its sweet.”  
“We’ve talked about this. Its just my face,” he teased as she glared at him.  
They reached the grand central station as they parted ways.  
“I’ll see you tonight?” she asked as her train reached the platform.  
“Yup. I’ll bring the party hats.”  
She smiled as the doors opened and she stepped in. She quickly poked her head out before he walked away and kissed him. As she pulled back and the doors closed, he gave her a small wave before the train finally departed.  
He wasn’t sure where this was going, but he was happy they were on the same page for once.  
———————————————————  
Jess, Matt, and Chris arrived at Dave’s party as it was just getting started. They didn’t recognize the majority of the people as they walked through the crowd except for random acquaintances they’ve seen at Dave’s shows. Jess saw Rory sitting at a table alone looking through her phone, as he approached her so did Laura and Oliver who he wasn’t expecting to see. He paused as Oliver sat next to her, extending his arm around her. He clenched his jaw and pursed his lips, unable to stop the tension that was rising in his blood.  
“Uh..is that a thing?” Chris asked.  
Jess didn’t answer as he stared at the couple at the table while Matt and Chris looked at each other with confusion.  
“Jess, we can sit somewhere else. Its cool. Lets not do this now..” Matt said placing his hand on Jess’ shoulder and steering him to a table parallel to Rory’s.  
As they sat down, Rory looked over at him with a look of shock. Jess did his best to give her his best neutral face and look away. He watched as Rory walked over to the bar to get a drink, dismissing Chris and Matt’s comments to leave it alone.  
He ordered a whiskey and coke as he sat down next to her. She looked at him as he sat down.  
“Hi,” she said looking to the bar, waiting for her drink.  
“Hi,” he said dryly, attempting to play it off.  
“So I meant to tell you..”  
“Tell me what?”  
“About..Oliver coming. About..us.”  
“Right.”  
“I’m sorry.”  
“Its fine.”  
“Its fine?”  
“Yup. Thats what I said,” he felt himself unraveling but it was too late to create the boundaries that he so desperately wished he had placed between them.  
“We aren’t serious. Him and I..”  
“Great.”  
“I’m not really looking for anything serious right now.”  
“Okay.”  
“Okay?”  
He looked at her finally, seeing her face of desperation, feeling like an idiot for thinking that this would go smoothly but remembering that Rory was a person that often contradicted herself.  
He nodded,”Yeah, we never really talked about this so I’m not holding it against you.” He gave her a small smirk, he wanted this to be okay, pushing his tension aside.  
“Good. Thats good,” she sighed giving him that familiar look of sympathy.  
“Well..I’ll be over there,” Jess said leaving back to his table before she could say otherwise.  
Chris and Matt turned to each other pretending that they weren’t trying to decrypt the scene before them.  
“Its fine,” Jess said sitting beside them and downing his drink.  
They looked at him and laughed, which in turn made him laugh. His life was a sequence of these events, at least when Rory was involved. He was glad they were there to witness how ridiculous it all was.  
Throughout the night Rory avoided Jess, or at least it seemed as such as every time he turned she moved farther away from him. He drank more trying to have fun with his circumstances.  
He was talking to Matt and Dave as Lane and Rory joined in on the conversation. He tried to ignore her as she sent him looks of concern.  
“Jess! I thought that was you!” Jess recognized the loud voice immediately as Isabel, a woman he went one a few dates with earlier in the year. She wasn’t exactly his type; loud, into yoga, a cat person, but he had fun with her regardless of their personality differences.  
“Oh uh hey Isabel,” he said awkwardly as she hugged him.  
She waved to everyone else in the group as they proceeded with their conversations.  
“If you’re not doing anything later, there’s a party going on down the street at the yoga place I teach at, I know its not exactly your scene but it’d be great to catch up with you!”  
“Oh sure. I’ll see,” he said giving her a smirk, noticing Rory staring at them from the corner of his eye.  
“Okay! Well see you later!” she said, giving him another hug before floating off into the crowd.  
Jess looked over at Rory who excused herself to go to the bathroom. He followed her as he saw her go out the door avoiding his eye contact.  
She was leaning against the wall as he walked out, she took out her phone in an attempt to block his gaze.  
“Hey,” he said standing next to her.  
“Hi,” she said still looking down at her phone.  
He turned to her waiting for her to look up at him.  
“What?” she said after a long pause, putting her phone into her pocket.  
“What’s with you tonight?”  
“Nothing,” she answered reluctantly.  
“Nothing?”  
“I’m just tired.”  
“Right. Tired.”  
“I can’t be tired?”  
“Yeah. But usually when you’re tired you don’t completely avoid me.”  
“I’m not avoiding you..”  
“Rory please.”  
“I’m really just tired.”  
“Okay..” Jess was frustrated, he felt like he was talking to a wall at this point.  
“Besides, shouldn’t you be going to see Isabel?” she asked with an emphasis on Isabel’s name.  
Jess scoffed,”Why’d you say it like that?”  
“Like what?”  
“Like she’s the worst person you’ve ever met,” he laughed.  
Rory’s face turned red,”I just didn’t expect you to be involved with someone like her.”  
Jess looked at her in defense,”Like her? what kind of person do you think I should be involved with?”  
“I don’t know. Someone with more substance, who’s smart, who you have things in common with.”  
Pursing his lips as he leaned his head against the wall,”Funny. You sound very judgmental of someone you don’t even know. Plus, I thought I did have someone like that but turns out I was wrong, she’s with someone else.”  
“Jess..”  
“No, you know what, I know I said I was fine earlier but I’m not. This is really fucking confusing for me Rory.”  
“I didn’t want this to be confusing.”  
“Really? because you seem to contradict yourself a lot. Why did you kiss me?” he was angry, this feeling had been pent up in him the whole night, over the course of six months worth of confusion came spewing out of him.  
“I’m sorry Jess but this is confusing for me too. I don’t..know how to feel about you. Its hard for me not to think about the past and how we fell apart and how hurt I was. Its hard to start new and you’re completely different now which makes this even harder. I can’t trust..this!”  
Jess’ face became blank, his anger being replaced with hurt,”You can’t trust me.”  
“No that’s not what I said, don’t put words in my mouth,” her voice was rising as she talked to him.  
“So I’ve changed and you still can’t trust me. What am I going to do, run away from you? I’m not, that’s why I’m trying to talk to you. But if you can’t even trust what I’m saying then what’s the point of this?”  
“Jess..” she moved closer to him and he moved away from her hand.  
Her faced dropped as her eyes filled with tears. He didn’t want to make her cry but he needed to put his defenses up, he hated that he let himself feel vulnerable with her again. He wanted to say more but as the words raced in his head Oliver walked out.  
He looked at him with anger,”Figures.”  
“Jess, wait,” she said desperately trying to keep him there.  
“Just..I have to go. So I guess you were right, I am running away from this,” he said giving her one last look before walking down the block. He used the last of his energy to not look back at her.


	7. Unmade bed

**Summary for the Chapter:**

> Jess and Rory finally make up for lost time.
> 
> WARNING: Lots of smut! ;)

The weeks following Dave’s birthday were dismal. Rory attempted to reach out to Jess, but he pulled excuses of being busy whenever possible and stayed out of the usual spots they would run into each other. As a last resort he told her he needed space, which he did, which kept her away.  
He hated this. He hated feeling like he was back at square one, that as soon as something happened between them it was inevitable for them to fall apart. He hated that he put himself out there again just for her to feel scared of him. He spent the morning chain smoking outside his office, staring at zine proofs that he wasn’t actually reading.  
“Hey man, you doing okay?” he heard Matt’s voice from behind him, wondering how long he had been standing there.  
“Yeah, I’m fine,” he answered back to you, not turning around.  
Matt sat by him on the stairs, taking the cigarette from Jess’ hand. Jess would otherwise be annoyed at this gesture, but in this moment he was grateful he had a friend to stop him from finishing the pack.   
“You should talk to her. Like really talk to her. Whether or not it has a good ending, you should at least get some closure,” he looked at Matt, taking in his advice and sighing.  
“I know. I should, but its…difficult. I already feel like an idiot.”  
Matt gave him a sympathetic smile,”Well sometimes, Jess Mariano, you have to put your pride and integrity aside to be able to talk to someone that you’re in love with.”  
Jess laughed,”Could you be any cheesier?”  
“Okay, I admit that was brutal, but you know I’m right. You’ve never gotten over her and if you plan on doing that now well..I really doubt you can unless you find out what you two could have..if you tried.”  
Jess sat there taking in the words that he knew he couldn’t get away from,”Thanks Matt..really.”  
“I’m really just sick of seeing you wallow all the time. It was cute when you were 21 but you’ve lost your charm,” he laughed giving Jess a nudge on the shoulder before walking back inside.  
Jess knew he couldn’t avoid his thoughts for much longer without completely blowing a fuse. He finished off another cigarette before delving into any decisions.  
————————————————  
It was a slow Monday morning at the shop and an especially hard one for Jess to get through since he spent the majority of the night thinking about how he would talk to Rory again. He re-read her last text message to himself over and over until the words became burned into his memory and he could see them in his eyelids.  
We can talk when you’re ready. I want you in my life, please don’t leave again.  
He did run away again. He should’ve fought harder that night, asked her to leave with him, completely ignored Oliver and actually said what they needed to. But he knew it wouldn’t have been that easy, that they did need time to think about what each other wanted. It was clear to him that he wanted her. He wanted her the first day that she walked into the shop, just like when he first saw her sitting in her bedroom in Stars Hollow. That night he went with Chris and Matt to a show at a bar in Queens, he was reluctant to go with them but he was tired enough that it didn’t taken him much convincing.  
It was during the first band that he saw her walk in. She didn’t look as miserable as he did, but he was pretty sure she could wear a paper bag and she’d still look amazing. She walked in with Lane and Dave and casually went to sit down not noticing him.   
He wasn’t sure how to play it cool since his anxiety had shot through the roof. It didn’t help that he wasn’t prepared to see her here and it was obvious that neither were Matt or Chris when Jess shot them glares harsh enough to make hell freeze over. He went over to the bar and sat there contemplating what to do next.   
“You have to talk to her,” Lane appeared next to him seemingly out of nowhere.  
“Hi Lane,” he said taking a sip of his beer and ignoring her suggestion.  
“Okay, be stubborn, I know you want to talk to her and I know she wants to talk to you so just do it already because we’re all sick of how much you two don’t know how to be together even though you’re soul mates and we all wish we had these issues over the span of ten years!” she was rambling and at that moment it was apparent why Rory and Lane had stayed friends for so long; they were just as neurotic as the other.  
“Okay. I’ll talk to her,” he humored her since he didn’t have the energy to keep up his front.  
“You will? Oh okay, good. That’s good. This is going to be good. I need to get back before she realizes I’m talking to you and you’re here,” Jess turned to her to say bye but was only met with an empty space beside him. He was wondering if he imagined it all or Dave had a point of her being a quiet runner.  
He walked up to their table as everyone quieted down and he gave a nod to Lane and Dave.  
“Hi,” he said unsure of how to proceed as he unsuccessfully swallowed the lump in his throat.  
“We’ll be…over there!” Lane said basically shoving Dave out of the booth towards the floor.  
Jess sat down and looked at Rory.   
“Hi,” she finally said quietly,”I’m..glad you’re here.” She gave him a small smile and looked just as nervous as he felt.  
The music started as Jess was about to reply, he gestured them to walk outside to talk instead. They silently sat down on a bench next to each other. Jess bit the inside of his cheek as he tried to find the words, anything, to be able to articulate the feelings he had pent up inside of him.  
“So,” they both said at the same time. He laughed that they were both unable to do this regardless of how long they’ve known each other.  
“I’m sorry. For leaving the other night instead of staying and telling you..everything,” he said finally looking over at her as she played with her fingers.  
She looked at him and he felt urged to continue before she could change her mind about their encounter.  
“I felt…really confused. I had all these feelings while you were gone that I couldn’t tell you about because I didn’t know how to tell you about them and seeing you again and..that kiss. It was overwhelming. And then seeing Oliver, I just don’t know..what you want from me,” the words jumbled from his mouth and he felt stupid again, but at least he was able to communicate something even if it wasn’t the most clear.  
“I’m the one who should be sorry. I always do this to you and you don’t deserve it Jess. Its been..amazing having you back in my life and I realized how much I missed you not being in it. I’m not scared of you, I’m scared about how I feel about you. We’ve always missed each other in one way or another that made it impossible for us to ever be..anything, but now we could do that and I fucked it up..”  
“You didn’t fuck it up,” he said quietly feeling her words sink into his skin.  
“I did. I really did. I don’t know why I invited Oliver the other night, I don’t like him at all, I honestly can’t stand hearing him talk for more than five minutes but he’s..comfortable. He reminds me of Logan and being with someone that basically has this life planned before him and is really predictable with everything he does. We have nothing in common and I don’t know, it was easy to blow him off. God, I’m an asshole,” she shook her head as she brought her hands to her forehead.  
Jess laughed,”You’re not an asshole. I don’t think you could ever be one of those.”  
“But I am! I always contradict myself and you’re right, I don’t know why I self sabotage everything that’s good—”  
“Rory.”  
“Like Yale and you helped me with that. And you helped me when I didn’t know what I was doing with my life after I was done at Yale a year later and I don’t know. I slept with Dean instead of just talking to you. I sabotaged this so many times.”  
“Okay but you fixed all of that.”  
“Yeah, but—“  
“No buts, if there’s anything I know about you is that regardless if you have some shit to figure out, you always do. Even if it takes you a questionable path to get to it, you do it.”  
They were looking at each other and Jess for the first time since their fight felt calm and relaxed, the throbbing of his heart subsiding from his ears.  
“You always forgive me. I don’t deserve that,” she said as she looked away from him.  
“You always forgave me and I definitely didn’t deserve it. You’re much better than a 18 year old who overdid the angst.” Rory giggled softly and Jess hoped she could still picture them back then as vividly as he did.  
“Jess, I want you. I know that I’ve wanted to be with you for a long time and I’ve tried so hard to fight that and I don’t even know why.”  
“I want you too,” he admitted it for the first time out loud and a weight melted off his shoulders.  
They leaned into each other about to kiss when Lane and Dave walked out as they moved away from each other,”Oh! I’m sorry, um we’re going to head home since the bands are done and we have work tomorrow morning…Rory are you okay to go home by..yourself?” Lane fumbled as it was apparent that she her lying skills had deteriorated as she grew older.  
“Yup. Goodnight,” Rory said as her face turned red.  
They said goodnight and gave Jess a wave as they walked away. Lane tried to conceal her excitement but Rory and Jess could hear her loud whispering all the way down the sidewalk. They looked at each other and laughed.  
They took the subway back to Jess’ apartment, grateful for an empty train as they sat silently together, Rory’s head on Jess’ shoulder. Rory reached for Jess’ hand and placed it on her lap, interlacing their fingers. He looked at her and gave her a smile looking down at their hands and examining how perfect their hands fit together. They leaned into the kiss that they waited for all night slowly deepening it as their tongues touched and Rory tugged on Jess’ bottom lip with her teeth. Jess put his hand on the back of Rory’s head to steady themselves in their seats, gripping a fistful of soft hair. He felt the vibration of her moan in his mouth and pulled apart from her partly to catch his breath and partly because they were in public. She smiled and bit her own lips that were raw from kissing, Jess stopped himself from proceeding further as they went back to holding hands through the last stops.  
————————————  
As they stepped through the door to his apartment, Jess had his nerves come back to him and hoped that this wasn’t the wrong move to make. They stepped into his kitchen for a glass of water as he felt the shared feelings of nervousness between them.  
They stood next to each other as Rory tugged on Jess’ jacket bringing him to her. He liked when she took control, especially since his hesitation kept him from giving into his lust for her. Part of him felt like he was back with the Stars Hollow Princess, virgin and pure, totally untouchable by the town’s thug. She pulled him towards her as they kissed again leaning against the counter, Rory’s tongue grazed Jess’ lips for entrance as her hand laced into his hair. He pushed himself harder against her, their kissing becoming more frenzied.   
He moved his mouth to her neck, finding the pulse point he used to suck on that would always make her squirm beneath him. He slipped off her jacket as she did his and they moved towards his bedroom trying not to trip on each other’s limbs. He knelt before her on the bed as he removed his shirt and hers in the process. She stopped him before her to touch his chest and run her hands over his abs slowly moving down and grazing the hard-on that was concealed under his jeans. His breath hitched at the contact and the look of pure pleasure on her face. She tugged him forward by the loop of his jeans so he was placed between her knees. Jess caressed Rory’s breasts through the light fabric of her bra before slipping her strap down her shoulder. He thumbed her nipple as it hardened and replaced his finger with his mouth. He tongued it lightly as Rory gasped to the sudden sensation. She moaned lightly as he nibbled on it. He removed her bra completely before giving the same attention to her other breast.   
Jess moved his hand up her thigh and under her skirt finding the damp cotton between her legs. He felt Rory’s breath hitch in his mouth as he moved her panties over with his fingers lightly touching her lips. He slid his index and middle finger between them, she was wet enough for him to glide down her center with ease, he clenched his jaw as his erection hardened further and his body ached. He rubbed her clit slightly which caused her to turn her head to moan breaking their kiss. He slid a finger into her wanting to hear her louder. Her legs closed around his hand as he moaned picking up his speed. Rory stopped him and he panicked for a moment hoping he didn’t make the wrong move. Instead she pushed him up to kneel before her again, unbuckling his jeans and tugging on him to take them off. He sat on the bed for a moment to take them off hastily and looked back to see Rory had already taken off her skirt. He went back to his place between her legs, only their underwear separating their skin. Jess leaned down and kissed her, deep and dirty, he couldn’t contain how much he wanted her. To be in her. He rubbed his erection against her center causing them both to moan at the friction, Rory bucking her hips forward in anticipation. He removed her panties quickly throwing them to the side as Rory simultaneously brought down his boxers. She brought her hand to his shaft, stroking it as his tip became wet. He looked at her as she bit her lip, he tried to steady his breathing but it was difficult to not completely lose it right there. He pushed her back as he sunk into her. Being inside her was overwhelming, they fit just as perfectly as their hands did.  
Jess thrusted into her slowly at first, kissing her as she wrapped her legs around his back. Their breathing quickened in unison as he sped up, he put one arm next to her as he moved forward slightly using his other arm to bring her leg to his shoulder deepening their friction. Rory moaned loudly causing him to deepen his thrusts further into her, he moaned as his abdomen tightened not wanting to come just yet. He let go of her leg instead hovering above her, letting their pelvic bones hit each other with each thrust. Rory was beautiful underneath him with a pained look on her face that matched his lust for her. She moved her right knee to his side making him lay on the bed as she got on top. She ground into him and he let out a muffled hiss at the change in position. He brought his hands to her hips, rubbing them over her breasts which bounced slightly as she moved. He sat up with her, pushing her hips to open farther as he took her breast into his mouth again, rolling her nipple with his tongue. Rory moaned against him as she quickened her speed gripping the bed frame behind Jess’ head steadying her to continue. Their breathing became shallow as it was replaced by a string of small moans as they both got closer to coming. Jess gripped Rory’s hip with one arm as the other steadied him onto the bed. He was close but wanted to see her come. He moved underneath her matching each thrust with his own until Rory brought back her head to moan loudly coming over him. As she tightened around him he came into her, moaning into her chest. 

They sat there for awhile, Jess still inside her as their skin glistened with sweat against the other’s. Jess caressed Rory’s face with his hand and brought her into a long kiss. They fell asleep in each other’s arms, bare, and covers on the floor. They woke up in the night and made love again; this time slower, but still filled with the need that they’ve had for over 10 years, making up for lost time.  
——————————————  
Jess was the first to wake up with no surprise. He looked at Rory, asleep and flawless as always. She was peaceful and he was hoping he was partly to credit for that. He moved his hand down her shoulder softly down to her hips, skin soft and smooth beneath it. She stirred as she opened her eyes.  
“Hi,” she said softly covering her mouth.  
“Hi, what are you doing?” he laughed putting his hand over hers.  
“I might have morning breath, don’t!”  
He moved her hand and kissed her.  
“Seem fine to me,” he smiled putting his forehead to hers.  
“So what’s a woman have to do to get some coffee around here?”  
“Little early for chauvinistic jokes don’t you think?”   
“You’re right, that was in bad taste, but its not my fault I’m not a morning person!”  
He laughed as he got up to put on his boxers and watched as Rory openly checked him out.  
“Are you checking me out?”  
“Of course. I can openly do this now and Jess you’re hot. There I said it, like you need an ego boost,” she threw his pillow at him.   
“I’ll go make some coffee,” he threw it back to her.  
He served them coffee and some toast to get through the morning, enjoying the site of Rory in his old Metallica shirt and panties.  
He cleaned up as Rory was sitting at the dining table reading one of the books on Jess’ shelves, he always wanted them to share a space together, reading books, being completely comfortable with one another. He walked over to her as she rose to meet him, giving him a hug and burrowing her head onto his chest. They looked at each other as Jess placed his hand on her jaw, his thumb rubbing her cheek. She moved her head so his thumb was over her lips as she brought it into her mouth and sucked on it up and down slowly. Jess exhaled sharply not realizing he was holding his breath. He moved his hands to her ass as he brought her onto the table and kissed her deeply, parting her knees. Rory moaned as she felt how hard he was against her, he took off her panties and lowered his boxers thrusting into her with more aggression than last night. Rory gasped against him and tightened her legs around him. He rode her hard, thrusting into her with no abandon. The books and various knick-knacks on the table toppled over and rolled off as Rory leaned back onto it to open her position wider. The table was rickety but Jess was glad it could hold them both long enough for him to get her there. He quickened his pace as she matched his movements, she moaned beneath him as she came, he wasn’t far behind as he came moaning into her mouth as she kissed him.   
They laid on the couch catching their breath, drifting in and out of sleep again. After a much needed rest period, they spent hours on the couch reading and eating the lunch that Jess made which included forcing Rory to eat more vegetables than she’s had in the past month.   
Jess was laying on Rory’s chest, book is one hand and the other playing rubbing her stomach.   
“We should probably shower at one point,”Rory said from behind her book.  
“Mhm,” Jess replied having put down his book and was moving between Rory’s knees.  
“What are you doing?” She asked, moving the book over to look at him.  
“Nothing,” he said while removing her underwear slowly.  
He sunk down kissing her stomach and the hair above her lips.  
“Jess..” she whispered as he moved his mouth, tongue sliding to her center.  
She exhaled as Jess placed pressure on her clit slowly moving his tongue up and down and sucking on the sensitive spots that made her legs shake. He brought her legs up to his shoulders as she moaned loudly. He inserted two fingers into her, reaching for her g-spot as he continued lapping at her, enjoying the view of her flushed chest and furrowed brow eyes closed in both pleasure. She reached down and tugged on his hair giving his a small smile. Her legs closed and Jess could only hear the rise of her pulse as he quickened his movements. She released him as she moaned, her legs shaking as she sprung forward coming hard. He moved up laying his head on her chest as she rubbed his scalp with her fingers.  
“Jesus,” she said finally.  
He laughed looking up at her.  
“Why are you so good at this? Actually don’t answer that.”  
“Because its you,” he answered regardless. He moved up to kiss her.  
“Maybe I should help you now,” she said while reaching down to feel the inevitable hard-on between them.  
“Its okay, it’ll go down eventually,” she kissed him cutting off his words and he moaned as she touched his head with her hand. She switched their position, Jess was laying down beneath her as Rory moved her way down between his legs. She moved his boxers down as her tongue licked up his length, not breaking eye contact with him.  
“Fuck,” Jess hissed.  
She brought his length into her mouth and began moving her head up and down. Jess closed his eyes as Rory opened up her throat taking in more of him; looking at her was enough for him to come right there but he wanted to appreciate this longer. She brought her hand to his shaft as she concentrated on his head with her tongue. He moaned and brought his hand to her head, grabbing her hair into his fist to get a better view of her. She looked at him and gave a moan causing a vibration in her mouth. Jess felt his abdomen tighten as he got closer to the edge. She moved faster in response to his shallow breathing, he bit his lip in anticipation.  
“I’m going to come,” Jess squeezed out, warning Rory in advance.  
“Mhm,” she kept going not taking her mouth off of him.  
He moaned as he came in her mouth, Rory swallowing and releasing his length as she wiped her raw mouth.  
He sighed as they laid together again, Rory’s head on his chest this time.  
“We’re never leaving this apartment,” she said matter of factly.  
“Doesn’t look like it,” he smiled as she kissed him.


	8. As long as we got

**Summary for the Chapter:**

> Does age bring ease or more heartache?
> 
>  
> 
> *Sorry its been so long! Had a lot of life stuff happen so I'm a little rusty. Just a short one to get this storyline going, let me know if there's any holes, I know it doesn't make the most sense but neither does anything aha

She left a couple of days after their first nights together, sent to Europe to cover what seemed like fruitless articles but ended up being much more, extending her stay to six months. Jess feels like he’s been left in limbo, having no solidified remains of a relationship in the wake of their passion. 

Its late October when they begin to talk more frequently again. She sends a simple email with one question

Any birthday plans?  
He stares at the computer screen and smirks, sighing with a shake of his head. He wants to be angry, but can only laugh, imagining Rory typing and erasing this message until she finally hits send. This is casual, regardless of his feelings he takes it as a omen to busy and strengthen the bubble he created around his individual life before she entered it. He spent the last couple of months writing something similar to a biography, telling himself its another novel focused on the weaknesses of a man, but his agent praises him and tells him to move forward. He writes consistently, constantly, effortlessly, and he hopes he won’t lose the drive if and when she comes back.

I haven’t thought about it.  
He writes back.

She’ll always be in the back of his mind.

He stays focused enough for Freddy to trust him to run the shop while he tours with Rush and Jess realizes more and more that the man is an enigma he will never fully grasp. He hires Dave to help him out, getting closer with him and Lane during the summer, being thankful that he has more than two friends; which is all he thought he could muster in his adulthood. Late fall always feels strange, the transition between fall and winter bittersweet. He remembers the harshness of his youth and Liz sending him away to Stars Hollow, unsure if it was a blessing or a curse. He thinks about what it would’ve been like it that didn’t happen if Luke hadn’t steered him in the “right” direction, if instead he let the city harden his bones and heart to the point of no return. He always thinks about this, every year, and wonders if the past effects everyone else as much as it does him. He pushes those thoughts away as he walks to therapy in early morning chill, the trees are beginning to bare, he breathes in slowly. He still needs this.  
————————————————————  
“You seem conflicted lately. From what I gather every week you’re always staying productive you aren’t necessarily stagnant in any way, what’s changed for you?” Dr. Finn sits across from him with his hands folded, on the table next to him is Jess’ folder filled with what he thinks is notes, progress reports, diagnosis chart, pieces of his vulnerable self.   
“I just keep having the same thoughts, like last year and the one before. My past keeps haunting me and I don’t know, its the same bullshit. I’m sorry, I feel like I always go in circles here,” he looks down at his own hands, unaware he was picking at a hangnail that’s begun to bleed.   
“We’ve talked about apologizing here, it’s not needed, that’s what you’re here for. To process. It doesn’t matter if we’ve talked about it before or whatever. The point is to get down to where and why this happens to you. Though I do believe you’ve been more stuck in your past recently, maybe because you’re around people from your past?”  
“You mean Rory?”  
“Rory, the friends you’ve met over ten years ago that you’ve built stronger connections with lately.”  
Jess stays quiet listening, contemplating change and its effect on him. He knew intimacy would change him, especially with someone so important. He wad never one to care if change happened, he was used to his turbulent childhood that was never stable, adapting to the constant fluctuations.   
“Regardless if the sudden changes are good or bad, you have to tune into how you’re feeling. A mechanism we’ve discussed thats difficult for you to overcome is guarding yourself from well, yourself.”  
————————————————————  
“I’m not dressing up for this.”  
“It’s Halloween! How can you not dress up?!” Dave argued from across the shop as he sweat before opening.  
“Because I don’t like Halloween.”  
“I get that. There’s some inherit connection to your childhood that you’re holding a grudge against but c’mon dude the house show will be worth it. Lane and I’s new band is tighter than ever. Do people still use that word? Well anyway, you can just put a “my name is God” name tag on and call it a night. Which is perfect since we all know you’re the Oz in our Buffy gang.”  
Jess stares at him with neutral unamusement, realizing that’s an Oz thing to do, and shifts giving him a small shake of his head.  
“Maybe.”  
“Alright, that’s progress!”  
They lapse into silence as Charles Mingus plays on the PA, Jess opens up the locked door hoping it won’t be another slow day.  
“So have you heard from Rory lately?” Dave asks while sorting through record columns.  
“Yeah actually, she sent me a one liner email asking about my birthday.”  
“Wait your birthday’s coming up?” Dave’s face lights up and Jess instantly regrets telling him.  
“Uh yeah on the 15th.”  
“What are you doing for it?”  
“That’s what she was asking. Probably nothing. Not really into my birthday to be honest.”  
“Okay so what are you into?”  
“Doom’s Day,” Jess deadpans.  
He goes to the side alley to eat his packed lunch on his break, smoking a cigarette and delving into Neil Gaimann, he’s gone onto reading as much sci-fi as possible, a genre he didn’t know he liked but he is his Uncle’s nephew. When he steps back into the shop, he finds Dave arguing with a group of bros on what is considered good nu-metal and decides to stay out of it sticking to manning the front desk while continuing his book.  
He gets up and steps in the middle of the group still well occupied,”Dave, you good? I’m gonna head to Truncheon for a meeting.”  
Dave waves him along as he ends up selling the entirety of the nu-metal section which Jess has no qualms about.

He steps out onto the sidewalk and lights a cigarette into the breezy air. He tried to quit various times over the last couple of weeks but the nicotine gum didn’t stick and he ended up tossing it out of frustration, finding the pack that he asked Dave to hide from him in the corner of the filing cabinet in the office. He figured if this was his vice and it hasn’t killed him yet, then it wasn’t that bad; at least thats what he told himself.  
Truncheon was busier than its been since it first opened. Stepping into the building, it sounded virtually deserted and he was glad that the rooms were renovated to be sound-proof before they even invested in it. He sat in the conference room, the reading room on special occasions, early for the meeting with his agent and the potential new writers he wanted him to meet. He pulled out the paperwork with their bios, he wasn’t entirely sure why his agent insisted on the meeting but he was learning to let others take the lead especially those who were helping him expand his career.   
Jeremy walked in shortly after with three people in suit; two brunette women and a blonde man who looked familiar. They sat down at the table as he introduced the group to Jess; Elise Skolter, Jennifer Redfern, and David Field. Jess immediately recognized David because he was the guy that Rory described as his doppelgänger, he did his best not to simultaneously roll his eyes and laugh, settling instead for a smirk that could be misinterpreted as a welcome smile.   
He sat as Jeremy ramble on about the prospect of a collection of short stories he thought would be a good opportunity for him, describing the intentional pick of these three people Jess has just met and never actually read and how their styles would work well together. He nodded when he thought it was the right time to nod, spacing out, and wishing this meeting would be over already.   
“Okay, sounds interesting,” Jess finally said after a pause he thinks might have proceeded a question.  
“Okay?” Jeremy reiterated sounding surprised.  
“Yeah, I like it, something new to Truncheon but it’d be a nice change of pace for me.”  
“Okay, wow great, I thought it would’ve been more difficult to get you to sign off on this, but great!” he continued with the logistics and paperwork that everyone signed off on, simple contracts and deadlines, whatever else went into the legal aspect of writing that Jess didn’t really care about.   
“Great well I’ll leave you all to get to know each other and see you at the next meeting in two weeks,” Jeremy exited hastily with a smile. Jess wasn’t really sure what he got himself into but hoped it was the kind of trouble that was at least fun to deal with.   
“Uh well I guess I can show you all around if you want..” Jess said awkwardly when he was met with stares after Jeremy left.  
“I’ve seen it, I was here for one of your readings recently,” Elise said quietly.  
“Oh thats awesome, I hope it wasn’t too cruel to get through for you.”  
“I’m a sucker for punishment so it was great,” she said with extreme wit, surprising him.  
“Perfect,” he smiled at her. He knew why Jeremy picked her.  
He went through each room with little detail, finally reaching Matt and Chris who he knew would takeover the tour as soon as they met Elise and Jennifer. He retreated to his office for some solitude, turning up the volume on his Lush album.   
He opened his email to a new one from Rory  
I miss you.  
He sighed again, closing the computer with a ache in his heart.  
————————————————————  
The end of October went by in an instant and the pit of anxiety that grows in Jess’ stomach as it nears his birthday grows bigger. Matt and Chris already plan his birthday in advance, a tradition they’ve done every year since they’ve known him and since they’ve moved back to the city they’ve been on an endless quest to find the perfect location. Jess did his best to ignore them, he was okay with the idea of celebrating as long as he was far removed from it as possible until the day of.   
(A regular argument that happened every year between Jess and Chris whenever he tried to reveal where they would take him)  
“So you don’t care if-“  
“No.”  
“But what if its at-“  
“No.”  
“Okay but what about-“  
“Jesus Christ Chris!”

The only birthday he ever enjoyed was when his mother was out of town and he spent the night out with some neighborhood friends sneaking into the community pool, stealing whiskey from a liquor store down the block, sleeping in a secluded spot in Washington Square Park; generally the birthdays that Liz were not around with whoever she was seeing at the time, whoever would whisk her away, so he wouldn’t have to see her substance abuse firsthand so he wouldn’t fear getting hit by another slacker boyfriend. It wasn’t until recently that they patched up their relationship as best they could, he still called her Liz, but she didn’t argue with him like she used to and she apologized for moments in time she remembered that he wanted to forget. He hates to admit, but if it wasn’t for TJ he doesn’t know where she would be; he also enjoyed having a little sister, getting to influence her slightly on her book choices even at her young age.   
He closed up the record shop for the day, even if it was a Friday, he figured he could partake in birthday excuses. He wrote a “Gone fishing, be back tomorrow” sign and stuck it to the front gate. He called off his meeting with Jeremy who was happier than he thought he would be, he figured that Matt or Chris told him how much he hated his birthday and all their plans for him since they loved to let everyone know. He went on with his normal routine of working out, going for a run, reading at Coffee Beans down the street - anything to normalize this day for any other day. 

“You’re gonna love it,” Matt said excitedly as they got out of their cab in Bed-stuy.  
“Cool,” Jess said with minimal enthusiasm.  
They walked down stairs to a basement style bar in the theme of Lovecraft. Dark, gritty, tentacle sculptures coming out of the ceiling with a giant Cuthulu head right above the bar. He remembers being in Portland while on his makeshift tour of the Subsect, stopping at a bar similar but not as refined as this one. He appreciated the effort they put into this, taking in the scene, happy there weren’t too many people around to feel bombarded.  
“We got the giant booths in back, figured you wanted your space, old man,” Matt patted his back as he ordered a pitcher of beer for the table.   
He heard her before he saw her. She was sitting at the end of the table talking to Lane, concentrated on their conversation.   
“Surprise,” Chris whispered to him. He could feel the knot in his stomach drop.  
She looked up at him,”Hi.”  
“Hi,” he smiled back at her.  
They moved into the booth to make room for everyone even though there was plenty of space.  
Rory was still smiling as he sat down next to her; a smile that told him “I got you.” He felt guilty for never emailing her back the last time.  
“What are you doing here?”  
“Its your birthday, of course I had to be here.”  
“Rory picked this bar for you!” Lane interrupted with uncontrollable excitement,”Sorry.”  
“Oh yeah?” Jess asked Rory.  
Her face turned red as she took a sip of her beer. He wanted to kiss her but wasn’t sure where exactly they stood, he kept casual by sitting by her with enough distance between them. She was wearing a deep red dress that hugged her body slightly, accentuating her curves even when sitting down, he tried his best not to stare at her even when her eyes seemed to gleam brighter blue than usual. He kept his distance for most of the night, trying his best to keep his composure even with the endless supply of drinks being handed to hum, he aimed to stay aware and clear, not wanting to make a complete drunken fool of himself.   
He went to use the restroom strolling down the long hallway between him and it, slightly staggering. He felt her fingers on his hand as he turned around to meet Rory’s eyes, still gleaming through the dark red lighting.   
“Hey,” she said with that smile she always gave him, one he never would describe but knew was especially for him.  
“Hey,” he said taken aback from her sudden body heat in front of him.  
“I just wanted to check in, make sure you’re having fun on your birthday, make sure its okay I’m here,” she rambled even when she didn’t mean to.  
“Of course its okay you’re here, it was completely unexpected, which makes sense for us I think,” he was also rambling when he didn’t mean to.  
She brought her hand to his face caressing his cheek and the scruff of his chin.  
“Sorry I didn’t email you back,” he finally said leaning into her touch.  
“I was hoping we would still have..this when I came back,” she said trailing her hand to the back of his head.  
“We always do,” he replied in a lower growl as he moved his hand to her lower back bringing her to him.  
He leaned against her forehead exhaling before moving into kiss her as she met his lips in unison. He leaned her against the wall as they intensified, tongues tangled together slightly just short of wanting more. He pulled away from her as he searched for the door handle to the bathroom. He opened the door giving her a nod to come inside with him. The bathroom itself was nicer than any he’s stepped into, too nice for a bar; it could be that or the black paint helped keep the illusion. She grabbed him after they locked the door behind them. Kissing him as they stepped back leaning against the sink’s counter. Jess moved his hands over her body with ease, listening to her breathing and interpreting her body language to make sure he could proceed. She took his hand from her face and moved it between her legs telling him exactly what she wanted. He moved more aggressively up her dress finding her center between the thin fabric of her underwear. She whimpered as he fingered her, he stifled a groan into her shoulder as she brought him back into a kiss. She unbuckled his jeans hastily as he slid her panties to her ankles and lifted her onto the counter. She pulled him to her locking him in with her knees, he pushed into her as they gasped at the contact. It didn’t take long to find his stride, each thrust more steady than the last, making sure to give attention to her lips and breasts in front of him.  
“Don’t stop,” she strained with desperation.  
He sped up pushing into her further, his breath shallow trying to control his movements. She moaned tightening her legs around him as she came, giving his last thrusts coming soon after. He placed his head on her shoulder as they tried to stead their breathing. He looked at her as she gave him a kiss.   
They smoothed their clothes, trying to hide evidence of their intimacy.   
“Maybe you should go out first,” Rory said smoothing her hair in the mirror.   
He looked at her, pushing aside the idea that she wanted to keep them secret.  
He nodded as she turned to give him a smile leaning against the counter they were just on.  
Jess returned to the booth with no one staring at him in suspicion, he took a long sip of the whiskey he left in front of him. Soon after Rory returned sitting by Lane on the other side of the table. He sat back into the cushioned back frame wondering what they were doing.


	9. Different Names for the Same Thing

**Summary for the Chapter:**

> So sorry for the huge delay! I had such writer's block with this story but the winter blues really helped out lol.   
> Hope this moves it along nicely!!
> 
> Questions are answered, holiday cheer ensues, Stars Hollow's quirks are unleashed

“I don’t think I’m going.”  
“What! Why not? You already missed Thanksgiving.”  
“So did you.”  
“Yeah but I was in Germany, you really have no solid excuses at this point.”  
“I was working.”  
“No one works on Christmas!”  
“I have been, the last three years actually.”  
“Don’t you want to spend time with Luke in snowy Stars Hollow?”  
“I can spend time with Luke literally any other day of the year.”  
She called him out of the blue the week before Christmas and they fell back into a bickering routine layered in flirtation as usual. She left the day after his birthday, it was early enough that he didn’t feel her leave his side at night, but the empty space next to him in bed still kept the shape of her. No questions were answered, instead he chose to normalize their situation, which most likely won’t last even if he worked on his patience every time he stepped into the therapy sessions.  
“So you’re not coming then?”  
“Maybe. I don’t know, I really have a deadline to meet with this book before the new year.”  
“Jess!”  
“Hey I’m leaving it at that, no promises, take it or leave it.”  
“God, you’re impossible.”  
“Yes, nice to meet you too.”  
He could see the look on frustration on her face and wished it were close enough for him to bring her into the prolonged kiss he’s been feeling since the last time they were together.   
He hated holidays, which was a surprise to no one, but he especially hated spending time in Stars Hollow this time of year. The last couple of years its melded every holiday throw-up you could think of; there’s a town scrooge that the children aide in reaching his Christmas spirit exorcism, there’s a Grinch that goes around harassing townspeople as they partake in watching the Jim Carrey version of its movie, truly there isn’t anything more he wished than Luke and Lorelai to move to somewhere less Twin Peaks/Dante’s Inferno. Plus, Lorelei has decided she’s obsessed with Christmas just last year and even Luke warned against him coming. Was he really going to sacrifice his dignity and sanity to see Rory? he hated that he was even contemplating making this decision.  
———————————————————————————  
“We’re moving the release back, now everyone can actually enjoy their holidays!” Jeremy exclaimed as his co-authors showed their excitement, he realized his last excuse was gone and Chris or Matt would easily rat him out if the opportunity came up.  
“You don’t look happy about this, don’t like the holidays?” Elise whispered to him.  
“Uh, not really, loathe would be a more appropriate feeling.”  
“Color me surprised,” she smirked at him as he leered back in her direction.  
The rest of the meeting, he spent spacing out since he had made more leeway in his portion of their collaboration than the rest of them have, spending the hour thinking about the upcoming week and preparing for the possibility of wearing an ugly Christmas sweater.  
“Are you coming to get a drink with us?”  
He awoke from his daydream, or rather nightmare, of viewing Kirk in a scantily-clad Santa outfit for Miss Patty’s birthday the last time he went to a Stars Hollow Christmas four years ago.  
“I don’t know, figured I’d get ahead and finish up what I have.”  
“C’mon, you’re already ahead of everyone else, let’s try to get the look of anger of your face.”  
“I’m not angry, that's just my face,” he smirked at Elise as he walked towards his office.  
“Just one drink! I think you could afford to be less of a Grinch, I don’t think it’ll hurt your reputation too much.”  
“Fine. But can David not come?”  
“Sorry, he’s the one that invited you,” she laughed.  
“Of course,” he scoffed as they walked outside to meet the others.  
Drinks were welcomed with ease since it was cold enough outside for your lungs to hurt. The week leading up to Christmas was busy for retailers but that meant the majority of Brooklyn stayed empty, which was Jess’ favorite part. The bar was no exception except for their group, which meant an endless supply of drinks with no wait.  
Elise placed a whiskey in front of him, “this is your drink right?”  
“I’m that transparent huh?”  
“Figured it fit your aesthetic,” she giggled as she took a sip from her beer.  
He took a swig while giving her a smug look back. He zoned out David talking up whatever he was trying to gloat about and instead drank enough whiskey to warm his insides. Elise sat closer and closer to him as the night went on, he didn’t reject her hand on his knee when she laughs or her arm laced in his. The others were sitting at the bar and he wasn’t entirely sure if this was all a set-up for this to happen.  
Her hand went up to the back of his head, her fingers running through his hair.  
“I like your hair longer,” she whispered next to him.  
He was looking straight as she talked to him, suddenly feeling a pang of guilt that he couldn’t shake. She brought her hand to his face and caressed his scruff as she met his eye contact, bringing her lips to his. She leaned into him slightly as he kissed her back, feeling the soft fabric of her dress against him. He broke away before they continued forward, remembering the pang in his stomach that was only slightly lulled by alcohol.  
Elise looked at him with concern,”Is something wrong? Maybe I was reading this all wrong.”  
“No. I mean, it's not you, I just..have someone. Sort of.”  
She looked at him in confusion before something clicked in her head,”Is it Rory?”  
He doesn’t remember ever mentioning her to anyone in their cohort but its possible during this strange night it might’ve slipped.  
“She’s come in remember? I’ve seen how much you feel for her. It's hard to miss.”  
“I really am transparent huh?”  
She smiled,”Its sweet. I’d say she’s lucky.”  
“We’re not really..anything,” he took a last swig of his drink to shut himself up, doubting she wanted to hear his aches.   
“Sure. You guys can tell yourself that,” she gave him a small pat on the leg before getting up to get herself another drink.  
It was nearly last call when they finally left, he couldn’t remember the last time he chose to go to bed at 5am or how much effort he’d put into another person, except for the last time Rory and him were together; in comparison, this time was different, he was trying to give his all and face his fears as best as possible, but were his efforts worth it?  
He dreaded the holidays the closer they neared.  
——————————————————————————  
He drove into town early enough that the square was empty and Luke’s had just opened up. The town was adorned with string lights, tinsel, ornaments on every tree branch and they managed to fit a total of 12 christmas trees for the tree-decorating contest by the gazebo. The snow covered everything in a blue glow and it was enough to make Hallmark puke from how perfect it all looked. He leaned against his car and smoked his first cigarette for the week, he managed to limit his intake enough the weeks prior to truly appreciate each drag. He looked on as he watched Kirk enter Luke’s with a green fur suit in hand, he tried to hold back his look of disgust. He also slightly looked forward to scaring Kirk off when he tried to Grinch him.  
He walked into Luke’s, giving a slight nod to his uncle as he sat at the counter.  
“You’re in early,” Luke said as he filled a cup of coffee in front of him.  
“Wanted to beat traffic,” he inhaled the coffee’s fresh-brewed smell in front of him, no coffee compared to Luke’s.  
“Eggs?” Luke asked acknowledging his common sense.  
“Sure.” He always appreciated their relationship and how little they could talk to each other without any concern for missed communication. What was once a struggle, now seemed natural for them.   
He brought out his book as he ate the eggs with spinach Caesar made him, listening to the soft Neil Young coming from the kitchen. He went upstairs when he was finished, laying down his bag and looking at the apartment around him. Luke had redone it as an act of anxiety before he married Lorelai and left it a completely different apartment than what he lived in as a teen. He hated to admit that he felt nostalgic for it, even when he slept on an air mattress for half of his stay.  
He walked downstairs as heard he the familiar voice of Lorelai carry over the diner.  
“Its the holidays and you’re telling me there aren’t any holiday specials?!”  
“I’m not going to take part in this,” Luke answered back in loving annoyance.  
“Rory demands some gingerbread french toast! She’s never in town and it's the least we could do for her.  
He stopped at the end of the stairs as she looked at him, giving him a small smile and wave. Act natural, he thought to himself and wondered what that even meant at this point.   
“Jess!” Lorelai yelled to him, ignoring Luke’s eye rolling as he walked back to the kitchen.  
“Hi,” he said as he stood awkwardly by their table.  
“Hi,” Rory said equally as awkward as Lorelai looked between them with a squint.  
“Some eerie deja vu in here…when did you get in? Liking the Bruce Springsteen look you have going on.”  
“Uh thanks. Couple hours ago. Had to beat the traffic out of the city.”  
“You could sit down you know. I think we’re at that level in our relationship, don’t you think?” Lorelai said pointing to a seat next to Rory.  
“Don’t want to interrupt, I was just going to wander around town for a bit. Take in the surroundings before the mayhem ensues.”  
“You might want to rest before facing the holiday cheer,” she insisted with her eyebrows raised. She had something up her sleeve but he couldn’t put his finger on it.  
He took the seat reluctantly, making sure there was a fair amount of distance between Rory and him. She stayed quiet as her mother talked on giving him a sympathetic look as her cheeks reddened in embarrassment. He tried to focus on Lorelai to keep himself from looking at her; her eyes became a striking shade of light blue this time of year, almost reflecting the snow around her, her hair a darker shade cascading from underneath her beanie, her cheeks and nose a permanent rose color.   
“So you should come!! It’ll be fun, I mean as fun as an entire tow fitting into the Inn and everyone probably arguing a wine bottle in.”  
He zoned out for too long and couldn’t recall what she had been going on about,”Sure, I don’t have much else going on.”  
“Great! Okay wow, I didn’t expect that for some reason but I could easily kick Kirk out of his room and give you it because he was going to really commit to his act and make this elaborate giant snow mountain to live in anyway. I think he’s probably just going home, but whatever. That’s some news, right Rory?” she nudged her as Rory gave a startled jump.  
“Which part? the kicking Kirk out or the entire town arguing over which cranberries were best?” she smirked faking her doze off.  
“Daughter of mine, so intuitive to everything around her,” Lorelai said with a big smile.  
Jess smirked, thankful that their relationship never changed.   
He parted ways from the diner, trying not to spend too much time around Rory even thought he had unknowingly agreed to spending a night in the same building as her, taking part in some town ritual that he already regretted.   
He sighed as he stepped out, already needing another cigarette. He walked down the block looking in each souvenir shop as people bought their last minute gifts, passing Taylor ignoring his protests against smoking in public.  
He stopped in front of the bookstore, with its fake snow spray-painted at the edges of each window and random train set moving in and out of stacks of books on display.  
“You have to applaud Andrew’s effort at decorating,” Rory said suddenly standing next to him.   
“Yeah, never took him for the merry type.”  
“Never took you for the merry type either. You’re really coming to the Inn tonight? heard there’s a hay ride in your near future,” she said smiling at him.  
He laughed,”I’m a regular ol’ George Bailey. Just when you think someone understands you.”  
“You surprise me every time I see you. I’m..glad you’re here.” She looked straight ahead as she talked to him. He glanced over at her and smiled.   
They went inside together perusing each aisle, he forgot how deep it went back, each section more and more crowded with books to maze through. they stopped at fictive non-fiction section that he didn’t question and looked through each title, wondering how the Hitchhiker’s Guide to the Galaxy made it in here. He felt the warmth of her ungloved hand as she laced her hand with his at his side, glancing over at him. He gave her a small smirk back, his heart jumping out of his chest as their eyes locked. They lean into each other with ease, Jess’ hand moving to the small of Rory’s back underneath her coat, she gasped softly at the sudden contact. Kissing her always felt like magnetism, he can’t help but be drawn to her, to let it consume him whenever they were together. She laced her fingers in his hair, gripping the strands underneath, he moaned slightly as her tongue touched his. They pulled apart when they heard a crash of books next to them but only saw the scurry of green fur run out of the aisle. Kurt was definitely not the worst person to catch them, but he knew that he never could keep a secret especially around Miss Patty and Babette. He looked at Rory and could not only see how nervous she was but she visibly pulled away from him.  
“Rory,” he whispered reaching his hand out to her.  
“I have to meet my mom at the Inn to help her out for tonight. Um, see you there?” she said with an awkward smirk.  
“Okay,” he stuffed his hands into his pockets, giving her a similar smirk back with a nod.  
She left hurriedly down the aisle and he didn’t look after her, but waited awhile to leave himself.  
He was a secret. He could feel the knot in his stomach tighten.  
————————————————————————————  
He spent the rest of the day before the inevitable Inn dinner in the apartment. He acted as casual as he could when he walked by Luke and Lorelai who acknowledged him with a wave as they continued their usual argument. The pit of his stomach felt like a pool of acid, he thought about completely ditching the festivities but he was determined to make it through the holidays, if anything for Luke and Lorelai who seemed to enjoy him being there.   
He laid down to drown out any noise from downstairs in his headphones, he didn’t remember dozing off until he woke up in the dimly lit room. It was 6pm on the dot, he slept for four hours, still feeling exhausted.  
Heading to the Inn. Feel free to show up casually late!  
The text from Luke seemed odd until he noticed the -L signed by Lorelai at the end of it. He sighed, looking through his bag for something decent to change into. He was going to be a spectacle regardless, might as well be presentable.  
He layered up for the trek outside since the snow had picked up as he slept. He settled for the usual black boots and black jeans, a worn in sweater over top with a flannel poking out. His hair was back to being long enough to not have to deal with it, he cursed to himself as he realized how much Lorelai’s comment reigned true.  
It was quiet out since every person in town was at the Inn, he could hear the crunch of snow under his feet as he walked, the roads only lit but christmas lights. His anxiety rose as he realized how unintentionally late he was, meaning he’d be the last one to arrive, meaning all eyes would be on him. He looked back at his car, his last chance to escape. Focusing on his exhaling breath fogged into the air, he kept walking forward.   
He could hear the music nearing, holiday twinkles and piano, thank god there was no caroling. He walked through the entrance and was engulfed in the lull of music and conversation, there were only slight murmurs from those around him at his arrival and he only hoped Kirk didn’t spill the beans from earlier. Though he’d love to punch the Grinch if he could.   
“Jess!” Lorelai yelled from the front desk.  
“Casually late, but not as cooly late as I expected, you literally haven’t missed anything yet,” she said as she signed in the other guests before him and took his coat.  
“Fell asleep. Bummed I didn’t miss at least the eggnog tasting,” he gave a slight scowl.  
“That’s one of the best parts! I mean it really ties in the experience,” he looked at her more closely as the other guests passed noticing her christmas sweater; a knit abomination with an embroidered chimney with boots hanging out the top, LED lights and too much sequin to focus on.  
“Nice sweater,” he laughed.   
“You should see the one Luke is wearing,” she gave him an evil smile.  
He looked across the room at Luke who was arguing with Taylor who was wearing the exact same sweater as him; from what he could see it looked like a mash-up of the Gremlins and camouflage, he applauded Lorelai for getting him to actually wear it.  
“Wow. You’re evil,” he smiled.  
“Isn’t the holiday spirit great! Anyway, here’s your key to your room, no pressure if for whatever reason you don’t want to stay, but I mean it's a lot nicer than the apartment and Luke told me your building back home has no heat so in comparison this is the Hilton.”  
“Thanks,” he slipped the key in his pocket. He brought his backpack just in case, but he was reluctant to stay the night, he needed to talk to Rory and wasn’t sure it would go well.  
He turned and found her glancing over at him from the other corner of the room talking to Lane who he had no idea was in town. He set for the stairs instead, opting for avoiding her for now. He passed the same group of giggling teenage girls he seems to always find when he’s in town who couldn’t look at him without blushing, it was going to be a long night.   
“Jess, hold on a second,” Luke said while he reached his room.  
“What’s up? Great sweater by the way, did you and Taylor coordinate on purpose or was that pure luck?” he tried to hold back a laugh as he took in the ensemble upclose.  
“Lorelai made me wear this okay, I’ve heard enough comments from her alone. Anyway, I got you a present, I know that isn’t really your thing but figured you’d rather get it now without the entire town snooping.”  
“Feel like that’s near impossible, but good call.”  
He followed Luke to his room where he handed him an album.  
“A photo album?” he looked at the worn-in burgundy leather cover, touching the embossed gold edges.   
“Yeah, it's something I held onto a long time. Has most of our family in it. Including a lot of baby pictures of you which I’m sure you didn’t know existed.”  
He looked through each page, organized by year, sparse but each page was filled meticulously with meaning.  
He found an old one of Luke holding Jess when he was little, he couldn’t have been older than 3 or 4. “Baby Jess and Big Uncle Luke” the handwriting was his mother’s, in the cursive of a teenager. He found a picture of Jimmy and Liz holding him as a baby, it must have been the only picture of all of them together before Jimmy left. He stared at it for a long time, he looked so much like Jimmy did back then, barely an adult.   
He felt a strange lump in his throat looking through these, at times when things were falling apart but held together by threads of family.  
“Thanks. I don’t know what to say,” he didn’t look up at Luke, transfixed with each old photograph in front of him.  
“You’re welcome. Figured you should keep it. I’m glad you’re here. Well uh, I’m gonna go help Sookie in the kitchen. Eggnog tasting is coming up, I’m sure you won’t want to miss Kirk heaving in the bathroom for the rest of the night,” he rolled his eyes just thinking about it.  
“Wouldn’t miss it for the world,” he closed the album finally, walking out with Luke. He set it in his room along with his belongings, he forgot how much effort was put into the Inn, how much of Lorelai shown through each room. For how much drama they went through in the past, he learned to appreciate and admire her, they were similar in a lot of ways.  
He closed his door and turned seeing Rory also exiting her room down the hallway. He froze, unsure of what to do, hoping she wouldn’t turn and notice him standing there deer caught in the headlights. She did in fact turn, almost mirroring his reaction until she gave him a small wave.  
“Hi,” she said over to him, visibly blushing.  
“Hey,” he said back as he walked over, even though it felt as though his legs were walking through quicksand.   
“So you made it I see,” she gave him a small smile but kept her arms folded.  
“Yup,” he said back.  
“Good, I was hoping you would come. I mean you said you would but it's still surprising you’re here. Not here at all, but staying for the holiday festivities,” she stumbled over her words and he just gave her a confused look.  
“Huh, less rambling than usual,” he quipped back at her.  
“I’m sorry, about earlier..”   
“No worries, you needed to help out your mom,” he knew that was a lie but didn’t feel like it was the right moment to talk to her about this.   
“Yeah..” she trailed off, biting her lower lip.   
“Well..I’m gonna head downstairs for dinner..” he said finally, the silence between them becoming unbearable.   
“Okay,” she said as he walked towards the staircase.  
“Jess,” she said after him.  
He turned towards her just as some town folk walked by them,”Yeah?”   
“Um, I’ll see you down there,” she said quickly, obvious that her choice of words were changed suddenly.  
He looked at her for a second before breaking their eye contact with a nod and taking the stairs.  
They needed to talk. But when?   
\-------------------------------------------------------  
The dinner was massive, there were enough entrees to feed a town twice the size of Stars Hollow, Jess was surprised that they could even fit at their tables with how much space the food itself took.   
He ended up sitting across from Rory which was both comforting and anxiety-inducing. He didn’t talk much because of how loud the conversations were around him, luckily Luke was also next to him, sharing the silence-bubble between them. Every once in awhile Rory and him would glance at one another, but not say anything. He wasn’t sure if this was a good front or suspicious to Lorelai and Luke, especially since Lorelai kept giving him this look like she knew they were up to something, but he was also unsure of that. He’d drank enough secretly spiked eggnog at this point, that it began to taste good and make him less aware of his senses.  
Lorelai tapped her glass with her spoon for a toast to begin the evening,”Hey everyone, I’ll keep this short and sweet but I just wanted to thank everyone for making this Christmas another one for the books. I truly couldn’t do it all without your enthusiasm! And personally I think there is no other way to celebrate Christmas without being in this town with all our loved ones, feeling those warm feelings of egg-nog inducing sentimentality. Anyway! Thanks! Keep eat as much as you can humanly stomach and more, because we will have enough leftovers to last us the rest of the winter at this point. Oh! Also it's time for the annual hayride, so gather your favorite person and take them for that small loop with possibly the slowest horse in the world…” at this point Jess zoned out, picking at the food on his plate remembering that hayride where he snuck onto Rory’s and he could feel himself falling for her. The feeling of deja vu was overwhelming.  
He looked up to find Rory staring at him, but she didn’t look away when he caught her, giving him a smile instead.  
“...I mean that's when I realized that Santa Claus was a fake. It really gave me some hope for my own future. Anyway! I love you all,” everyone clapped as Lorelai finished her speech and sat down to finish her third plate of food.  
Everyone went outside to get on a carriage, but Jess decided to stay back to smoke a cigarette in solitude at the back of the Inn where he could barely be seen.  
Snow was falling sparsely over him, illuminated by the streetlight above. He was slightly drunk, turning the cigarette in his fingers, feeling each snowflake melt upon contact with his skin.  
“Not going on the hay ride?” Rory asked suddenly next to him.  
“No one to go on it with,” he said matter-of-factly, sticking the cigarette back in his shirt pocket.  
“That didn’t seem to stop you the last time,” she joked back at him, confident in her words.  
“Different times I guess. Not as bold this time around,” he looked at her, locking eyes.  
“I wish you would be,” she said to him, he swallowed that lump in his throat that formed again.  
She pulled him to her by the brim of his jacket. He clenched his jaw, unsure if he should let himself proceed without talking to her. But he couldn’t get the words out before they were kissing again, the world stopping around them, their breath visible between them, heat radiating off each other.   
He pulled away, getting back to reality,”I...can’t do this anymore.” His own words surprised him.  
“What?” Rory asked with hurt already written on her face.  
“I can’t pretend this doesn’t bother me anymore. What am I to you Rory? You pulled away from me earlier and could barely be seen with me in public, be seen talking to me like you do when we’re back home. I..don’t want to be a secret.”  
“Jess..”  
“No, this isn’t fair. Changing your mind about me is one thing, but stringing me along--”  
“I’m not trying to string you along--”  
“Then what?” his frustration grew with each passing minute, he breathed in trying to pause enough for her to explain.  
“I’m scared okay. I know that’s not an excuse. I know I said that months ago. I’m scared for this to go anywhere because it might just fall apart again.”  
Her words felt like punches even if they weren’t intended to be.  
“I think we’re both different now, don’t you think? I’m not going to leave you Rory.”  
“How do you know that? We’ve never been stable.”  
“What are we now? Is this not worth it to you? To at least try again?”  
“I...don’t know. I can’t..shake this feeling off just like that.”  
“You can’t trust me. It's been over ten years and you can’t trust me still..”  
“Jess, that’s not what I’m--” she reached for his arm but he backed away this time. His face hardened, masking the acid he could feel building up.  
“Maybe you’re right. Maybe this was a mistake and we shouldn’t have gone down this road again. God knows I’m bound to become my father and leave as usual.”  
“C’mon, that’s not fair,” she scoffed as tears welled up in her eyes.  
“It..doesn’t matter. I want you, I want to be with you, but that doesn’t seem to be what you want,” he looked at her trying to find the answers he was looking for but only being met with tearful sympathetic eyes.  
“I’m sorry, I didn’t mean to-” she strained the words, tears rolling down her face as reached up to wipe them away quickly.  
He nodded, feeling his own tears well up, biting his cheek to keep his emotions in check.  
“Right,” he turned away pausing before heading back inside,”I’m done..”  
“Jess,” her words ached out heavy with sadness.  
He didn’t turn back around, quickly heading towards the stairs to his room to grab his backpack and head back to the apartment. He snuck out while Luke and Lorelai were by the carriages, helping patrons pair up.   
The snow was falling heavier now, he wouldn’t be able to leave town until the morning, which he’d hope he could do with ease. He could see Rory now, crying telling her mother of their secret affair and how he broke her heart again. Being cast as the villian time and time again. He sat by the open window, letting cold air in as he exhaled smoke out trying to find the release of how empty he felt. He chain-smoked one after another until he made it through half the pack finally rubbing his eyes and realizing it was 2am. He looked down at his phone, seeing the text from Luke  
Are you back at the apartment? Call me.  
He missed a couple of calls from him from a couple of hours before. He threw his phone against the wall behind him, hearing the crack of its impact and its fall.  
There was a sudden knock on the door, it was soft enough for him to almost believe it was his imagination. He got up slowly, staring at it with confusion. The knock came again, this time slightly louder. He walked towards it, still wondering if it was real.  
He opened the door to find Rory silhouetted against the dark hallway behind her. He looked at her and only felt his heart jump. She was wet, just as much as he was from walking over in the snow without a jacket. They stood in front of each other until he moved his arm to let her in.   
“What are you doing here?” he said in a harsher tone than intended when he closed the door.  
“I don’t know. I mean..trying to tell you something I should’ve said hours ago. Years ago..”  
He looked at her, still standing by the door, half wishing he would’ve left in the white of night. He waited as she mustered up whatever it was she needed to cast him down with.  
“Remember when you showed up in Stars Hollow after coming back from California? And I had no idea until you avoided me all day and then chased me around town until you finally caught up to me?”  
The memory appeared vividly in his head as she recalled the memory out loud, he nodded wondering where this was going.  
“Remember when you told me you loved me and then left?”  
He nodded again with a little more hesitation.  
“Why didn’t you wait for me to say anything back to you?” she looked at him, eyes strained from crying, lips red from chewing.  
“I..was scared you didn’t love me back..” he said, his own tears welling up again.  
“Well..I did love you,” exhaling before she continued,”I still love you Jess..”  
A stream of tears fell down his face before he could stop them. He exhaled, his heart racing in his chest. She moved in front of him, slowly bringing her hand to his face, wiping away the remnants of his tears, “I love you,” she repeated looking into his eyes.  
“I love you too,” he whispered out to her.   
She laid her head on his chest as he wrapped his arms around her.


	10. Ready for the pageant

**Summary for the Chapter:**

> Small inbetween chapter, just because it was a funny scenario I needed to get out of my head.
> 
> Everyone knows! Lets all just imagine Jess in his underwear now

Jess woke up the next morning with Rory still in his arms. He squeezed her closer to him as she let out a small sigh against him. He felt less heavier than he did the night before, the empty space in him finally feeling fulfilled. He kissed her neck and she whimpered slightly, squirming against him.   
“Wake up,” he said in her ear.  
“Mmmm,” she replied to him.  
“Please,” he nibbled on her ear.  
She let out a small gasp, rolling over to face him, giving him a kiss. He grazed her face with his hand and brought her into a deeper kiss before moving his hand to caress her bare breast. She moaned in his mouth at the contact. She pulled away to get some air.  
“What if someone hears us?” she breathed out.  
“Isn’t Luke’s always closed on Christmas? I think we can buy some time before anyone realized we aren’t at the Inn,” he moved his free hand over her curves.  
“Hm good point,” she said back as she pulled him on top of her. They had only their underwear separating them as Jess’ hard-on rested between her thighs, she wrapped a leg around him boring him into her, he let out a sharp exhale at the contact.  
“You’re gonna kill me,” he smiled.  
“I’m not done with you yet,” she smiled back kissing him again.  
They made love, the build-up from the night before fueling their eagerness for one another, their need for one another.   
\-----------------------------------------------------------  
Rory laid her head on his chest, their breathing slow and in sync.  
“This was nice,” she said coyly with her eyes closed.  
“Oh yeah,” he smiled, a full smile for once, the one he reserved for her.   
“Coffee?” she asked looking up at him.  
“Yeah, sounds like something you should have at...almost 11 in the morning. Jesus its late.”  
“Oh no,” Rory said as she looked over at her phone, “my mom called me so much last night and left an indecipherable text at 4am, probably sleep texting.”  
Jess got up and changed back into his underwear, slipping a shirt over his head.  
“She’s probably still sleeping right? I mean you guys aren’t morning people and its Christmas, should be okay.”  
“I’m sure I’ll hear something or other when we head to the house together later.”  
“Together huh? Not your dirty little secret anymore?” he joked at her, but she nudged him annoyingly.  
“No! Never were, I feel like today is a good day to reveal you to the world. You’re ready for the pageant,” she laughed.  
“Hm you need coffee,” he dodged another nudge from her as he handed her one of his shirts to wear.  
They headed downstairs still reeling from their morning together, Jess teasingly grabbing at her butt as she stepped in front of him.  
“Stop!” she hissed as they moved from behind the curtain together. They looked up to an almost full diner, stopping in their tracks caught in front of Luke who also stopped to stare along with the rest of the customers. Rory immediately ran back behind the curtain before Jess could react in time, he slowly backed his way up the stairs too.   
“I thought Luke’s was closed today!” he yelled as he closed the door behind him.  
“It is! I mean it’s supposed to be!” she yelled back in a panic, putting on the rest of her clothes.  
“Clearly it isn’t, I think half of the town was in there,” he rubbed his face hoping he’d snap out of this.  
“Ughhh!!” Rory replied in frustration.  
“Well that’s one way to tell everyone we’re together I guess?” he tried to shine light on the situation but was only met with a death glare.  
Luke burst in just then and they jumped apart akin to their teen years. He stood there in the doorway with his hand still on the handle without saying a word, he looked almost as embarrassed as they did.  
“What is going on here?” he finally asked when he closed the door behind him.   
“Hm uh well..” Jess struggled with words and trying not to pull a joke to relieve the tension before Luke continued without the explanation.  
“So first you two completely disappear last night leaving us worried sick thinking something ridiculous happened to you in this godforsaken town, having Lorelai barely get her 10 hours of sleep and now you come downstairs nonchalantly…” his expression changed from anger to confusion to what looked like happiness,”Are you two together?”  
Jess opened his mouth to try to string along a round-about way of answering his question but Rory answered with a simple,”Yes.”   
He looked at her and smiled as she took her hand, interlacing their fingers. His nerves loosening as she gripped his hand lightly.  
“Oh..well..that’s great. Really, was I the last one to know about these this?”   
“You’re the first one..and half of the town,” Rory gave a small laugh lined with misery remembering the look on everyone’s faces.  
“Wait, why aren’t you closed today?” Jess finally asked.  
“I was going to be, but we wanted to change things up this year, give people the option to spread out today. It was Lorelai’s idea, I couldn’t care less.”  
They all stood awkwardly around trying to figure out how to proceed.  
“Uh I have to get back down there. Did..you want breakfast?” he gave a shrug.  
“Uh sure,” Jess replied, not sure how they would casually step back into the diner now that everyone has seen him in his underwear.   
“Okay. Great. This is really great,” he nodded giving them a smile before heading downstairs again.  
Rory and Jess looked at each other, still holding hands and laughed because of course this would happen to them in this town.  
“You ready?” Jess said before opening the door again.  
“Guess we have to go down there at some point,” she gave a concerned face.  
“Hey, it’ll be okay,” he reassured her and kissed her on the head closing the door behind them.


	11. Together

**Summary for the Chapter:**

> Sorry for the long delay! Hopefully this closure is worth it <3
> 
> Christmas miracles aren't always where you expect them

Jess woke up the next morning with Rory still in his arms. He squeezed her closer to him as she let out a small sigh against him. He felt lighter than he did the night before, the empty space in him finally feeling fulfilled. He kissed her neck and she whimpered slightly, squirming against him.   
“Wake up,” he said in her ear.  
“Mmmm,” she replied to him.  
“Please,” he nibbled on her ear.  
She let out a small gasp, rolling over to face him, giving him a kiss. He grazed her face with his hand and brought her into a deeper kiss before moving his hand to caress her bare breast. She moaned in his mouth at the contact. She pulled away to get some air.  
“What if someone hears us?” she breathed out.  
“Isn’t Luke’s always closed on Christmas? I think we can buy some time before anyone realized we aren’t at the Inn,” he moved his free hand over her curves.  
“Hm good point,” she said back as she pulled him on top of her. They had only their underwear separating them as Jess’ erection rested between her thighs, she wrapped a leg around him boring him into her, he let out a sharp exhale at the contact.  
“You’re gonna kill me,” he smiled.  
“I’m not done with you yet,” she smiled back kissing him again.  
They made love, the build-up from the night before fueling their eagerness for one another, any worries falling at the wayside.   
\-----------------------------------------------------------  
Rory laid her head on his chest, their breathing slow and in sync.  
“This was nice,” she said coyly with her eyes closed.  
“Oh yeah,” he smiled, a full smile for once, the one he reserved for her.   
“Coffee?” she asked looking up at him.  
“Yeah, sounds like something you should have at...almost 11 in the morning. Jesus it's late.”  
“Oh no,” Rory said as she looked over at her phone, “my mom called me so much last night and left an indecipherable text at 4am, probably sleep texting.”  
Jess got up and changed back into his underwear, slipping a shirt over his head.  
“She’s probably still sleeping right? I mean you guys aren’t morning people and its Christmas, should be okay.”  
“I’m sure I’ll hear something or other when we head to the house together later.”  
“Together huh? Not your dirty little secret anymore?” he joked at her, but she nudged him annoyingly.  
“No! Never were, I feel like today is a good day to reveal you to the world. You’re ready for the pageant,” she laughed.  
“Hm you need coffee,” he dodged another nudge from her as he handed her one of his shirts to wear.  
They headed downstairs still reeling from their morning together, Jess teasingly grabbing at her butt as she stepped in front of him.  
“Stop!” she hissed as they moved from behind the curtain together. They looked up to an almost full diner, stopping in their tracks caught in front of Luke who also stopped to stare along with the rest of the customers. Rory immediately ran back behind the curtain before Jess could react in time, he slowly backed his way up the stairs too.   
“I thought Luke’s was closed today!” he yelled as he closed the door behind him.  
“It is! I mean it’s supposed to be!” she yelled back in a panic, putting on the rest of her clothes.  
“Clearly it isn’t, I think half of the town was in there,” he rubbed his face hoping he’d snap out of this.  
“Ughhh!!” Rory replied in frustration.  
“Well that’s one way to tell everyone we’re together I guess?” he tried to shine light on the situation but was only met with a death glare.  
Luke burst in just then and they jumped apart akin to their teen years. He stood there in the doorway with his hand still on the handle without saying a word, he looked almost as embarrassed as they did.  
“What is going on here?” he finally asked when he closed the door behind him.   
“Well..” Jess struggled with words and trying not to pull a joke to relieve the tension before Luke continued without the explanation.  
“So first you two completely disappear last night leaving us worried sick thinking something ridiculous happened to you in this godforsaken town, having Lorelai barely get her 10 hours of sleep and now you come downstairs nonchalantly…” his expression changed from anger to confusion to what looked like happiness,”Are you two together?”  
Jess opened his mouth to try to string along a roundabout way of answering his question but Rory answered with a simple,”Yes.”   
He looked at her and smiled as she took his hand, interlacing their fingers. His nerves loosening as she gripped his hand lightly.  
“Oh..well..that’s great. Really, was I the last one to know about this?”   
“You’re the first one..and half of the town,” Rory gave a small laugh lined with misery remembering the look on everyone’s faces.  
“Wait, why aren’t you closed today?” Jess finally asked.  
“I was going to be, but we wanted to change things up this year, give people the option to spread out today. It was Lorelai’s idea, I couldn’t care less.”  
They all stood awkwardly around trying to figure out how to proceed.  
“Uh I have to get back down there. Did..you want breakfast?” he gave a shrug.  
“Uh sure,” Jess replied, not sure how they would casually step back into the diner now that everyone has seen him in his underwear.   
“Okay. Great. This is really great,” he nodded giving them a smile before heading downstairs again.  
Rory and Jess looked at each other, still holding hands and laughed because of course this would happen to them in this town.  
“You ready?” Jess said before opening the door again.  
“Guess we have to go down there at some point,” she gave a concerned face.  
“Hey, it’ll be okay,” he reassured her and kissed her on the head closing the door behind them.  
\-------------------------------------------------  
They walked back into the diner, still hand in hand waiting for some sort of protest at their companionship but were met only with glances, everything back to (mostly) normal.   
Luke placed two cups in front of them filling them with coffee. They obliged sitting side by side with their knees touching slightly. Luke placed Jess’ usual in front of him and three usuals for Rory’s three stomach-appetite. Jess shook his head, he was in love with her and all her quirks. They openly gave each other longing looks between their bouts of talking about the books they were reading. Luke looked over from the register with a smile on his face, finally he thought.  
“What gives! You didn’t return my calls last night and here you are eating breakfast without me and Jess with his stupid vegetables acting like he isn’t part of this somehow-” Lorelai exclaimed angrily as she walked over to them.  
“Lorelai, wait,” Luke started standing in front of her, trying to get her under control and loosen the eyes of every patron in the diner waiting on the unfolding drama in front of them.  
Lorelai moved around him with ease and he looked at her with amazement at her sudden grace, quickly following behind her.  
“Mom, I-” Rory started.  
“I’m not done being angry here. Rory, I didn’t want to spend Christmas Eve worrying about you, wondering where the hell you went off to. Which wouldn’t be a lot of places in this one bridge town but thats not the point, where were you?” she continued, her blue eyes glaring, Jess felt as if the gaze was directed to him and he wasn’t even the one receiving the angry rant for once.  
“Jess,” Rory said quietly.  
“Jess what?” Lorelai said drawing the glare to him, enough to make him feel chills.  
“Jess. I was with Jess. We were here together. We’re together..” she blurted out, exhaling the nerves she was hanging onto.  
“You were with Jess?” she said confused looking from Rory to Jess back to Rory.  
Her face softened as she pulled Rory into a hug.  
“Finally,” she said holding onto her.  
“What?” Rory muffled into her shirt.   
She pulled Rory back, her hands at her shoulders,”I mean I knew this but you’re telling me now and finally we can all just stop acting like you two aren’t together.”   
She smiled at Rory and Jess who both gave her a confused smirk back.   
“So you’re okay with this?” Jess asked quietly.  
“Despite how I once thought of you, yes. I love this Jess. I love this Jess with my Rory,” she said giving him a genuine smile, Jess could feel a lump tightening in his throat completely taken aback by her words. Rory stood by him taking his hand in hers again.  
“Next time, could you guys for the love of god just let someone know so Mommy doesn’t have a heart attack,” Lorelai said as Luke wrapped his arm around her waist.  
“I’m sorry mom.”  
“Well let’s make Christmas less overwhelming and move this to our house shall we? Leave the diners to back in the really uneventful result of this debacle.”  
“Sounds good to us,” Rory said looking over to Jess who couldn’t stop his smile.  
\----------------------------------------------------  
“Coffee?” Lorelaidasked as she poured a cup for her and Rory.  
“I’m good, I don’t think I could drink anymore without getting heart palpitations,” Jess replied.  
“Oh you have Luke’s weak heart,  my condolensces,” Lorelai joked as she sat down beside him.  
“Yeah I’ll never see the bottom of a coffee carafe, its a real tragedy,” he quipped back. Rory smiled into her mug, revelling at the two people she loved enjoying each other’s company. Jess placed his hand on her knee under the table, lightly caressing it as they all talked.  
Lorelai began taking groceries out of the fridge to start preparing for dinner, leaving both Rory and Jess staring at her with their mouths wide open.  
“What?” she asked giving them a look back.  
“Who are you and where did you take the real Lorelai Gilmore?” Rory asked.  
“So I decide to cook one year and everyone thinks its the Hindenburg disaster?”  
“Or you’re carrying Satan’s child and you’ve been possessed,” Rory says back.  
“Ugh I’m insulted! I just really wanted the first year that Luke and I had together as an official married couple to be special. You two being here makes it all the more reason for me to put more effort in this than going to Al’s Pancake World and hoping they have gravy included in their mystery package,” she scoffed.  
“Okay maybe we shouldn’t have been as surprised but I really don’t remember the last time we made anything in this kitchen..do you need any help?”  
“From you?” Lorelai laughed.  
“Now I’m insulted!” Rory laughed back.  
Jess just shook his head, secretly loving being around their ridiculous relationship.  
“I can help. I mean if you need to avoid any Hindenburg tragedies..” he offered genuinely.  
“See your help I do need. You’re experienced in the kitchen and obviously Luke handed his genes down to you, I mean look how you’re sitting!” she handed him a cutting board and a bag of vegetables. Jess sat perplexed noticing his jiggling foot resting on his knee with one arm rested on the chair’s shoulder. He stopped and sat up straight.  
“Only if you never mention that again,” he said getting up to join her on the cutting board.  
She crossed her heart and handed him some vegetables. Rory sat at the table with a book in hand, smiling at the two of them.  
\-----------------------------------------------  
“Wow its as if we didn’t spend five hours trying to finish this before Luke got home,” Lorelai said while throwing out the evidence of their work.  
“Yeah, cleaning while you work, what a concept?” Jess joked helping out.  
“It smells amazing in here!” Rory said while ringing out her wet hair after a shower. She was wearing only a fluffy robe, Jess found it hard not to check her out openly while Lorelai was around. She looked at him and blushed.  
“Hopefully it tastes as good as it smells,” Lorelai said while scrambling to put on her coat.  
“Where are you going?”   
“I need to grab some things for dessert and stop by Luke’s to see if he needs any help closing up so he can hurry up and get here while my Christmas spirit is still alive,” she replied hastily putting on her boots.  
“Do you guys think we need anything else?” she asked before going out the door.  
They both shook their heads even though she didn’t bother to hear their reply.  
“This is weird,” Jess said after a moment of silence.  
“Yeah..I’m ready for the Christmas spirit to die, but excited to eat all the food you prepared for me,” she said smiling and bringing him to her.  
“Just for you,” he said while kissing her.   
He opened her robe to reveal her complete lack of clothing, she gasped slightly on her hands grazing her stomach.  
“How long do you think we have till she comes back?” he asked while places kisses down her neck.  
“Awhile,” she whispered back bringing their lips together for a deepened kiss.  
———————————————  
“Hello! We’re back! Here’s a warning so you can save any dignity you have left from us!” Lorelai said as she yelled into the house, a mumbling Luke behind her.  
Rory and Jess were sitting on the porch out back, leaning against each other as they read. They had enough time to get redressed and mask any evidence of their afternoon escapades. Jess wonders if their spark will ever settle, but he wasn’t exactly complaining.   
“Oh you’re out here, good,” Luke said bursting through the back door.  
“You really need to relax when you open doors,” Jess said looking up from his book.  
“Sorry, habit,” Luke rolled his eyes back at him.  
They followed Luke in to find the table already set and candles ready to be lit while A Christmas Story played on TV.   
“I know its still light out but the mood needs to be set,” Lorelai said while lighting each candle.  
“Yes the Christmas mood,” Jess said dryly, Rory trying hard to hide her smirk.  
“You know liking you is something I can change,” Lorelai said smiling at him with a wince.  
“Right. Sorry, habit,” he said with a smirk, causing Luke to glare at him.  
They sat down and Jess half expected there to be a prayer before dinner, relieved that they just all dug in instead.   
“Wow, this is..amazing,” Luke said with surprise.  
“Really good,” Rory nodded.  
Lorelai smiled,”Thanks to Jess.”  
“Oh no, I helped-“ he began.  
“No, you really helped, you made basically everything and I really appreciate it. Take the praise in, get used to it,” Lorelai said while eating her mound of food.  
“Thanks,” he said awkwardly, still not used to any sort of appraisal from her.  
They chatted casually and ate as much food as possible, moving onto the pie that Luke had brought home. Everyone moved onto the couch to watch to the rest of A Christmas Story, Jess putting his arm around Rory who placed her head on his chest. He felt happy, which is something he couldn’t place for a long time, but only knew how to describe when she came back into her life. He felt lucky that this was his life now, that this was solidified and in the flesh. He exhaled as Rory sneezed him looking up at him with a smile. He kissed her forehead, feeling at peace.  
He helped clear the table and wash dishes when the movie ended, Luke joining him soon after. They shared a silent agreement together, working side by side without a word.  
“Wow, you guys are quick,” Lorelai said as she cleaned off the rest of the table. They both nodded.  
“And very chatty. Well, its early but I feel like I ate an entire turkey, which I guess I almost did, so I think I’m going to go to bed,” she said sleepily placing her head on Luke’s shoulder.  
“I might join you in a bit. If you feel this tired from food, we should all be in a coma by now,” Luke replied drying off his hands.  
“Go ahead, I can finish up,” Jess said taking over the dishes.   
“You sure? You really don’t have to, you did cook earlier,” Lorelai said with a surprised look.  
“Its fine really,” Jess said firmly in reassurance.  
“Wow you are the Grinch. But at the end where his heart grows three sizes bigger and he’s holding hands with all the townspeople and singing along.”  
“I’ll make sure to steal some lawn gnomes to protect my reputation. Goodnight,” he laughed as Luke moved Lorelai along upstairs.  
He finished placing the leftovers in their tupperware and found Rory on the couch having fallen asleep with a book in her hands. He wanted to give her the Christmas present he brought her, but her peaceful face kept him from waking her up. He slowly took the book out of her hands and sat next to her, she instantly leaned her head against his shoulder. He smiled as he picked up the book he was reading earlier and read until he couldn’t remember falling asleep himself.   
———————————————  
Jess woke up in daylight, still on the couch with Rory huddled with her head in his lap. He fell asleep sitting down, feeling his back ache as he moved positions to place her on the couch. He stood up to give a good stretch, trying his best to remain quiet as he went upstairs to take a shower.   
As an adult he reduced his showers to 10 minute increments, which was considerably more manageable than the hour he would take an a teenager. He walked downstairs drying his hair, carefully placing each step on each stair avoiding the creaks. He looked over at the couch and didn’t see Rory. He rounded the corner looking into her old room, her silhouette against the sunny window sitting looking through a stack of books. Reminiscent of the moment he first saw her, she turned giving him that same look with her electric blue eyes almost always piercing him. His heart beat hard in his chest as it did then, he could feel his love for her surging through his body.  
“Hi,” she smiled at him.  
“Hi,” he smiled back, still standing in the doorway.  
“You can come in you know, you didn’t used to hesitate so much,” she joked at him.  
“I guess it feels more taboo now. There isn’t the risk factor anymore,” he laughed. Her room was almost the same as he could remember it, minus it was gutted from all its college paraphernalia and Luke painted it a soft cream color when he was renovating the rest of the house. Most of her books were at her place but some still lived on the shelves, he assumed ones she lined with memories of Stars Hollow.   
She sat on the bed, patting the spot next to her. He sat down next to her as she leaned her head against him, he wrapped his arm around her shoulder bringing her closer, placing a kiss on her head.   
“Its weird isn’t it? You being here and my mom not trying to chase you out of my room. Not that she did the times you visited in the past, but I’d say the hostility isn’t there anymore,” she smiled looking around the room.  
“Yeah really going to miss her death glare, now she has me cooking for her,” he laughed looking at her.   
She brought them into a kiss, her hand tangled into his hair, he could smell the scent of strawberries in her hair.   
“I like this,” she whispered between them.  
Luke and Lorelai peeked in quietly before moving into the kitchen,”Usually I would make some sort of witty comment to break that up but they’re so sweet. And usually I would gag at this moment, but I really like this.” Lorelai quietly remarked her enthusiasm as they made coffee. “Me too,” Luke wrapped her in a hug, smiling at his nephew’s happiness.  
——————————————————————  
Jess walked out to his car after lunch at Luke’s, he packed up his small bag ready to go back to the city, feeling much more whole than he did when he got here. Rory was going back to the UK in the morning, leaving for another month but this time was different - this time they were together so her arrival back was more anticipated than ever.   
“So you think you’re going to leave just like that huh?” she said as she walked out to the car.  
He put the cigarette that was in his hand back in his pocket, smiling at her eyes reflected ten-fold by the cloudy white of the sky.  
“Figured you’d come out here eventually,” he smirked at her as she grabbed his hand.  
“I’m gonna be gone for a month…I..don’t want to go,” she said eyes glossy from tears looking down at their feet.  
He brought her closer to him, embracing her in his arms,”Hey, I’ll be there when you get back,” he looked at her in front of him, wiping the tears before they fell. They kissed softly, entangled in front of his car door, the bitter-sweetness of their goodbye.  
“Well, if the town didn’t know before, they definitely know now,” he joked as they parted.  
“Good,” she said giving him one last kiss.  
“I love you,” he said loudly after her as she walked back to Luke’s.  
“I love you too!” she yelled back with a smile.   
He watched as she went in, turning on the engine preparing for the drive home.  
It was their home now.


	12. hello stranger

**Summary for the Chapter:**

> Its been such a long time! Because of that, this is mostly filler and a lot of sex to make up for it ;)

“So I received this little present in the mail. Totally indiscript, loosely wrapped,” Rory said over the background chatter of airline announcements.  
“Oh yeah? Should I feel threatened by this present?” Jess smiled as he shifted through papers in the office of the record shop.  
“I would be. Its beautiful. A pure sapphire pendant on what looks like real gold. The person who sent this must really like me,” he could hear her smiling through her words and the fluttering in his stomach couldn’t resist.  
“Sounds like it...I’m glad you got it safely. I was worried you wouldn’t get it in time for your flight.”  
“Its beautiful, Jess. It was worth the wait and the suspense of it possibly being a present for the hotel staff to fawn over.”  
“I can’t wait to see you,” he said with honesty, a concept he was glad he could communicate as he matured.  
“I’m assuming you’ll be at the airport at 6am with bells on,” Rory giggled.  
“How about we meet at Ruth’s and I buy you breakfast at 7:30? I wake up early but even you won’t get me to an airport at that time.”  
“Fine, I guess I shouldn’t have assumed you would lift the highest mountain for me just yet.”  
“I mean, that I could do, going to JFK during early morning commuting hours, never. Not even if Bruce Springsteen made an appearance there.”  
Rory laughed, glad she was put on the same caliber as the Boss himself. They finalized their plans, Jess left to watch each hour pass by in anticipation for her arrival.  
“You sure you’re cool with taking over tomorrow? I can always come by in the afternoon,” Jess said over to Dave as he took his place at the register.  
“And have you and Rory basically making babies in front of customers? No thank you, I got it,” he joked as Jess gave him a death stare across the room.  
“Besides, don’t you have news to tell her?”  
“I guess, it's not the biggest deal, I don’t want to make her first day back about me.”  
“Jess, it’s a HUGE deal! You have a literal book tour in Europe! This is big.”  
“It's honestly more stress than it's worth and I’m not sure I want to go through with it, so what’s the point of telling her,” he shrugged not looking over at Dave’s disapproving frown.  
“Are you serious? You’re serious, of course you are, but you can’t be stubborn with this, this is a huge opportunity for you man. If anyone’s going to be supportive, it’s Rory. You don’t have to worry about that.”  
“We just got together and I’m constantly worried I’m going to fuck up…” his honesty maybe taking over more than he’d like to admit.  
Dave walked over to the counter with full attention,”I’m a little taken aback with this Jess, but I’m not hating it. Now, I will say that is 100% bullshit. You haven’t fucked up whatsoever, also you’re a human, also shut the hell up she’s in love with you,” Dave smacked his fist onto the counter to accentuate his point.  
Jess sighed, knowing that Dave was right but the weight of negativity only lifting slightly.  
He didn’t sleep much that night, waking each hour staring at the clock just waiting for his alarm to go off. Dave’s words looped in his head, he kept thinking of how far him and Rory have come but how many times he had left her. How could he leave when they were just starting to stabilize their relationship?

He woke up suddenly, not even remembering when he fell back asleep. His clock glowed 7:15 launching himself up from bed immediately. He threw on whatever clothing he could shift through and ran out the door. He hailed a taxi and hoped he wouldn’t keep her waiting for too long, his sleepy daze replaced with anxiety.  
Walking through the doors of Ruth’s gave him the similar feeling he would get when he walked into Luke’s; a nostalgic sentimentality he couldn’t explain. “Hello Stranger” played on the jukebox, it almost felt like a staged scene in a movie about lovers.  
He saw her sitting in the corner and everything slowed down, he gulped the invisible lump in his throat that was fueling his thumping heart. She was engulfed in a book, her eyes only looking up when she finally felt his presence. Her face flashed a bright smile, her eyes illuminated by her blue blouse.  
“Hi,” he said as she got up from the booth to hug him.  
“Hi,” she replied as her face sunk into his neck.  
He exhaled the breath he was holding, his senses replaced with the smell of her strawberry shampoo.  
They exchanged one prolonged kiss before sitting across from each other with no words. Rory’s cheeks already flushed with color.  
“I’m sorry I’m late, I slept through my alarm, weird fluke. Hope you weren’t waiting for too long,” he exhaled again, the words flowing jaggedly, still flustered with seeing her.  
“Strange for you,” she flashed her smile again and he couldn’t help but smile back at her.  
“Yeah, couldn’t fall asleep fast enough I guess I was anxious,” he admitted looking down at his fidgeting fingers.  
She reached across the table with her hands covering his,”Its okay, I was able to catch up on more reading and give my heart time to stop palpitating out of my chest.” She laughed, biting her lip.  
“Glad it's not just me,” he caressed her fingers with his not breaking eye contact with her, afraid she’d disappear like in their past.  
Jackie, the waitress walked up with a smile, “Jess! It's nice to see you and who is this beautiful sugar?” she said with a thick southern accent.  
“Hi Jackie, uh this is Rory,” he blushed slightly unsure if he should introduce her as his girlfriend.  
Rory reached out her hand in a hearty handshake powered by Jackie’s enthusiasm, “So nice to meet you honey, he’s told me so much about you.” She smiled as Rory looked over at him with her eyebrows raised.  
“Good things I hope. It's nice to meet you.”  
“What can I get you? It's on me today!”  
“You really don’t have to,” Jess insisted, breathing through the excitement of the last five minutes.  
“Yes I do. Any lady of yours deserves the special treatment, you’re a handful,” she deadpanned as she wrote down his usual of a spinach omelette with a black coffee.  
“I’ll take the classic with a extra side of hashbrowns and the cheesecake french toast. Oh and a bowl of fruit and lots of coffee, maybe two cups to start,” Rory said while giving back her menu.  
Jackie’s eyes grew big with disbelief, “A little thing like you?”  
“I’ve learned not to question it,” Jess laughed.  
“Mhm, well I’ll be back shortly,” she said while serving them coffee, taking Jess’ advice.  
“So this is your Luke’s,” Rory said while sipping from her mug which resembled a soup bowl.  
“Close enough. I don’t come here too often,” he sipped from her normal-sized cup.  
“You’re lying! She knows you by name, how many times do you come here? Three, four times a week?”  
“Two, maybe three times, shut up!”  
“Its cute, you really love Luke so much you needed your own diner,” she teased him.  
“I’m a man of habit and nothing more,” he rolled his eyes with a chuckle.  
“Okay Luke,” she teased him further.  
“Ew that’s your dad now,” he laughed.  
“Shut up!!” she nudged him with her foot.  
He looked at her, finding that love in her eyes he always searched for when they were younger. His heart was full and he knew it was time to tell her.  
“So.. I have something to tell you,” he started.  
She put down her mug to give him her full attention, knowing this wasn’t a usual sly comment of his.  
“I was offered to go on a book tour for our collected stories we’ve been working on since last year. It's not even done yet, but they want us to leave in the next couple of months while everything is finalized to be able to hit the ground running with it..” he paused looking up at her trying to gauge her reaction. He was only met with a smile, her hands extending out to him again.  
“Jess, that’s amazing!! Where’s it going to be? Across country again or local?” she asked as he waited for his thoughts to catch up to him.  
“Um, Europe actually, completely international this time,” he bit his lip as he looked at her, her face only slightly disappointed.  
“That’s..amazing! Really…for how long?” she asked, this time with less enthusiasm. His heart began to sink into his stomach.  
“That’s what Jeremy is trying to figure out. He’s thinking three months, hoping for six,” he said with a heaviness on “six.”  
“Jess, this opportunity is so important,” she said feeling his doubt.  
“But we just…got this together. We’re together and you’ve been gone for so long, I don’t want to leave this.”  
“I’ll always be here for you when you get back, we know we can make it through this. You’ve been doing this with me so patiently, of course I’ll do the same for you. I love you,” she gave him a smaller smile, her eyes twinkling with the sun shining against her. They haven’t exchanged that word since he yelled it from the street at her in Stars Hollow, the words floating between them but only now becoming more real.  
“I love you too,” he said as she squeezed his hand.  
“It's funny actually. I was offered another four months of traveling, but decided to stay here this time.”  
“Rory..”  
“No it's fine, I’ve honestly been so tired and it’d be great to have this place be my home finally and build a clientele here.”  
She reached over at his face, he leaned against her caress kissing her hand.  
“We’ll be okay, we’re a team now. I want you to do this,” she said with only a slight doubt in her eyes.  
Jackie walked over with their various plates of food, “You sure you don’t need more hands for all this?”  
“She’s a professional, trust me,” Jess said while Rory squinted at him.  
They ate together, pushing aside the conversation at hand that wasn’t entirely done instead talking about what Rory had seen and done while she was away, the sights he hopes to see when he travels. He nodded along, still unsure he could leave her for so long, leave them for so long again.  
They walked down the street with his arm around her as they kissed, reminiscent of their teen years where they would almost always walk into oncoming traffic.  
“We’re going to get beat up by people trying to actually use the sidewalk,” she said as he continued to engulf her.  
“It’ll be worth it,” he smiled with mischief.  
“We won’t be able to kiss when we’re dead!” Rory said while exchanging their stance for hand-holding instead.  
“Have you read Romeo and Juliet?!” he exclaimed, admitting defeat. She rolled her eyes as she trailed them into a bookstore.  
Rory teases Jess by dodging each lustful look and hugs from behind as they search the aisles of the bookstore, virtually empty just for them. He watched her as she read the synopsis to The Dispossessed by Ursula Guin, giving her a puzzled look.  
“You reading a science-fiction novel for once?” he questioned.  
“What? I’m trying to expand my palate, weren’t you the one trying to get me to read all of Atwood?” she rolled her eyes.  
“Just didn’t think it was possible with how stubborn you were with your taste. It took so many years for you to admit Ayn Rand was problematic.”  
“Problematic?! Says the man who loved Ernest Hemingway!”  
“I grew out of it!”  
She rolled her eyes even further when Jess slapped the book out of her hand.  
“Real mature!” she nudged his arm.  
He grabbed her, bringing her into a passionate kiss. She brought her hand into his hair as he eased his under her shirt, causing her to whimper at his touch. He leaned them against the bookcase as he intensified their kiss.   
They stopped at the sound of someone clearing their throat in front of them, looking over with ruffled hair and embarrassment, deer caught in the headlights.   
“Can I help you find anything? Or do I need to kick you two out for indecent exposure?” the older man asked in possibly the snarkiest New York accent Jess could think of.  
He was about to give back an equally snarky answer until Rory intervened, “We’re sorry, we were just leaving. Thank you, your store is amazing, really love the extensive philosophical apocalypse theory section,” she smiled as she grabbed Jess by the hand and rushed them out the door.  
“Oh my god,” she finally said with her hand to her reddened face as soon as they reached the outside.  
Jess held back a laugh, biting his lips.  
“It's not funny! We’re not in highschool anymore, he could’ve called the cops on us!” she exaggerated.  
“I’m pretty sure he has to do that with people actually committing indecent exposure in his store,” he smiled at her, releasing the laugh he held in just a moment before.  
He grabbed her again, “Plus, it was worth it.”  
“There’s the bad boy charm I fell in love with,” she deadpanned as she gave him a kiss.  
“So...we’re pretty close to my place--”  
“Yes,” she cut him off, which only furthered his longing for her. They tracked down a cab since Rory was still towing her luggage from the airport.   
In the back of the cab, they held hands remaining quiet as they pictured their afternoon together. Rory unlaced their fingers, trailing her hand up Jess’ leg. He clenched his jaw as she settled on his crotch, slightly rubbing him through his jeans. They both looked out the window, looking inconspicuous to their actions. Jess did his best to hide how turned on he was by Rory’s dominance.   
When they reached his apartment, he didn’t bother to say hi to Dave as they passed by the shop, only faintly hearing Rory and him exchange quick greetings, determined to get them upstairs. Each time they didn’t see each other for months, he felt as if a growing pain ache in his stomach, only relieved when he was able to feel every inch of her inside and out. He unlocked the door and looked at Rory with lust before picking her up over his shoulder.  
“My bags!” she exclaimed laughing.  
He squatted down without letting her go to grab her bag with his other hand while kicking the rollybag with his leg, kicking the door closed on their way in.  
“How could I forget how hot and muscular you were?” she smirked as she grabbed him into a kiss, his arms embracing her around her lower back. They kissed blindly until they reached the edge of the couch, Jess leaning his forehead on hers as he took her shirt off, unable to catch his breath. She took off his shirt just as quickly returning to his lips as he lightly ran his hand over her bra reaching for its hook. He took it off with ease, his nerved relaxing as he He kneaded her soft skin as he teased her nipple, his hardon restraining against his jeans. She moaned as she pushed against his body, moving them onto the couch so they could gain stability.   
She positioned him so he was sitting as she knelt down in front of him. She didn’t break eye contact as she reached for his zipper, biting her lip in concentration. Jess felt like his limbs were paralyzed, encapsulated by the woman before him, a trance he always fell prey to when she took control. He moved up a bit as she pulled his jeans over his knees, teasingly placing her hands over his boxer-briefs. He hitched his breath followed by a moan as she brought his cock out rubbing the shaft up to the head as she watched him flinch. She kissed her way up, still maintaining her hard gaze as her mouth encircled him slowly moving down his length. He moaned louder as he clenched his abdomen, lacing his fingers into hair. She moved up and down with precision, knowing just the right amount of force and speed to get him off, he struggled to keep control nearing dangerously close to the edge. She sped up just as he stopped her, moving her onto the couch next to him. He nudged the rest of his jeans off, returning to her lower half, almost ripping her skirt off altogether. He he opened her legs, hovering over her body as he traced down her stomach towards her center. Rory flinched as his fingers reached between her lips, teasing her clit, Jess moaned into her hair at the realization of how wet she was underneath him. He kissed her as he sunk two fingers deep inside her, her walls closing around them. He pulled them out slowly at first as he simultaneously rubbed her clit, listening to each sound she made, waiting for her pitch to get higher and higher.   
“Jess, I want you,” she whispered as she grabbed his hand.  
He didn’t hesitate before taking off her panties and throwing them to the side, noting their laciness for later. He moved her down as she brought her hand back to his cock, rubbing it against her clit a couple of times causing him to hold his breath at the pleasure. He sunk into her as they moaned together, finally becoming one. He thrusted into her hard, not hesitating to gain speed, their foreplay initiating a buildup he ached to release. She hooked her legs around his torso as he drove into her, their sounds in harmony to each other’s contact. He changed their position, looking for the deepest penetration, his want turning to a need. He flipped her over, her hands clenching the armrest as she moaned louder, his pelvis driving further into her. He held onto her hips as each thrust neared them to climax. He sped up feeling the clench of her walls around him, she let out a loud cry as her body began to relax under him. He thrust a few more times, cumming into her with muffled moan into her back. They stayed there, him still inside her as they breathed in trying to regain their surroundings. He withdrew himself slowly sinking into the couch as she melted next to him, her head leaning against his shoulder.   
“You’re wild,” she said matter-of-factly.  
As he could do was laugh as he put his arm around her and kissed her head.  
“Glad to be of service,” he said with confidence.  
She let out a loud breath as she closed her eyes against his chest.  
If it's one thing they’ll never have trouble with, its their passion, their need, their growing want.

**Author's Note:**

> This is only the first chapter, there's a lot to build upon!


End file.
